Essendon lead Sydney 135–97 with 1 draw in 233 games since 1897. They have met once in a Grand Final; Essendon won the most recent, in 1912. Their last meeting, in the 2026 Round 23 at the MCG, went to Sydney by 36 points. They next meet in the 2027 Round 2, Sun 28 Mar 2027, 3:15pm AEDT.
Sydney's record includes games played as South Melbourne (1897–1982). Source: Wikipedia: Sydney Swans.
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 2026 16 Aug | Round 23 | Essendon | 11.10 (76) – 17.10 (112) | Sydney | MCG | Sydney by 36 |
| 2025 2 Aug | Round 21 | Sydney | 9.14 (68) – 7.12 (54) | Essendon | SCG | Sydney by 14 |
| 2025 10 May | Round 9 | Essendon | 11.5 (71) – 8.15 (63) | Sydney | Marvel Stadium | Essendon by 8 |
| 2024 16 Aug | Round 23 | Essendon | 8.11 (59) – 15.8 (98) | Sydney | Marvel Stadium | Sydney by 39 |
| 2024 23 Mar | Round 2 | Sydney | 19.17 (131) – 15.11 (101) | Essendon | SCG | Sydney by 30 |
| 2023 29 July | Round 20 | Essendon | 15.9 (99) – 15.11 (101) | Sydney | Marvel Stadium | Sydney by 2 |
| 2022 2 July | Round 16 | Essendon | 15.5 (95) – 12.14 (86) | Sydney | MCG | Essendon by 9 |
| 2022 14 May | Round 9 | Sydney | 14.21 (105) – 6.11 (47) | Essendon | SCG | Sydney by 58 |
| 2021 1 Aug | Round 20 | Essendon | 16.6 (102) – 17.7 (109) | Sydney | MCG | Sydney by 7 |
| 2021 8 Apr | Round 4 | Sydney | 11.17 (83) – 12.8 (80) | Essendon | SCG | Sydney by 3 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 2017 9 Sept | Finals Week 1 | Sydney | 19.7 (121) – 8.8 (56) | Essendon | SCG | Sydney by 65 |
| 1999 5 Sept | Finals Week 1 | Essendon | 18.15 (123) – 7.12 (54) | Sydney | MCG | Essendon by 69 |
| 1996 21 Sept | Preliminary Finals | Sydney | 10.10 (70) – 10.9 (69) | Essendon | SCG | Sydney by 1 |
| 1942 12 Sept | Preliminary Finals | Essendon | 19.10 (124) – 14.12 (96) | Sydney | Princes Park | Essendon by 28 |
| 1924 20 Sept | Semi-Finals | Essendon | 10.12 (72) – 4.15 (39) | Sydney | MCG | Essendon by 33 |
| 1923 29 Sept | Semi-Finals | Sydney | 10.14 (74) – 8.9 (57) | Essendon | MCG | Sydney by 17 |
| 1912 28 Sept | Grand Final | Essendon | 5.17 (47) – 4.9 (33) | Sydney | MCG | Essendon by 14 |
| 1912 14 Sept | Semi-Finals | Essendon | 7.12 (54) – 6.6 (42) | Sydney | MCG | Essendon by 12 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 2026 16 Aug | Round 23 | Essendon | 11.10 (76) – 17.10 (112) | Sydney | MCG | Sydney by 36 |
| 2025 2 Aug | Round 21 | Sydney | 9.14 (68) – 7.12 (54) | Essendon | SCG | Sydney by 14 |
| 2025 10 May | Round 9 | Essendon | 11.5 (71) – 8.15 (63) | Sydney | Marvel Stadium | Essendon by 8 |
| 2024 16 Aug | Round 23 | Essendon | 8.11 (59) – 15.8 (98) | Sydney | Marvel Stadium | Sydney by 39 |
| 2024 23 Mar | Round 2 | Sydney | 19.17 (131) – 15.11 (101) | Essendon | SCG | Sydney by 30 |
| 2023 29 July | Round 20 | Essendon | 15.9 (99) – 15.11 (101) | Sydney | Marvel Stadium | Sydney by 2 |
| 2022 2 July | Round 16 | Essendon | 15.5 (95) – 12.14 (86) | Sydney | MCG | Essendon by 9 |
| 2022 14 May | Round 9 | Sydney | 14.21 (105) – 6.11 (47) | Essendon | SCG | Sydney by 58 |
| 2021 1 Aug | Round 20 | Essendon | 16.6 (102) – 17.7 (109) | Sydney | MCG | Sydney by 7 |
| 2021 8 Apr | Round 4 | Sydney | 11.17 (83) – 12.8 (80) | Essendon | SCG | Sydney by 3 |
| 2020 14 June | Round 2 | Sydney | 11.7 (73) – 12.7 (79) | Essendon | SCG | Essendon by 6 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 2019 6 July | Round 16 | Essendon | 11.10 (76) – 9.12 (66) | Sydney | MCG | Essendon by 10 |
| 2019 10 May | Round 8 | Sydney | 11.11 (77) – 10.12 (72) | Essendon | SCG | Sydney by 5 |
| 2018 27 July | Round 19 | Essendon | 15.19 (109) – 10.6 (66) | Sydney | Marvel Stadium | Essendon by 43 |
| 2017 9 Sept | Finals Week 1 | Sydney | 19.7 (121) – 8.8 (56) | Essendon | SCG | Sydney by 65 |
| 2017 23 June | Round 14 | Sydney | 11.20 (86) – 12.13 (85) | Essendon | SCG | Sydney by 1 |
| 2016 7 May | Round 7 | Sydney | 20.15 (135) – 7.12 (54) | Essendon | SCG | Sydney by 81 |
| 2015 4 Apr | Round 1 | Sydney | 10.12 (72) – 9.6 (60) | Essendon | Stadium Australia | Sydney by 12 |
| 2014 1 Aug | Round 19 | Sydney | 11.13 (79) – 8.9 (57) | Essendon | SCG | Sydney by 22 |
| 2014 16 May | Round 9 | Essendon | 9.10 (64) – 18.6 (114) | Sydney | Marvel Stadium | Sydney by 50 |
| 2013 1 June | Round 10 | Sydney | 17.13 (115) – 10.11 (71) | Essendon | SCG | Sydney by 44 |
| 2012 9 June | Round 11 | Essendon | 11.16 (82) – 13.8 (86) | Sydney | Marvel Stadium | Sydney by 4 |
| 2011 6 Aug | Round 20 | Essendon | 15.10 (100) – 14.15 (99) | Sydney | Marvel Stadium | Essendon by 1 |
| 2011 3 Apr | Round 2 | Sydney | 14.14 (98) – 13.15 (93) | Essendon | Stadium Australia | Sydney by 5 |
| 2010 6 June | Round 11 | Sydney | 12.17 (89) – 12.8 (80) | Essendon | SCG | Sydney by 9 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 2009 11 July | Round 15 | Sydney | 10.12 (72) – 15.17 (107) | Essendon | SCG | Essendon by 35 |
| 2008 18 May | Round 8 | Sydney | 21.17 (143) – 7.10 (52) | Essendon | Stadium Australia | Sydney by 91 |
| 2007 2 June | Round 10 | Sydney | 11.7 (73) – 11.8 (74) | Essendon | SCG | Essendon by 1 |
| 2006 5 Aug | Round 18 | Sydney | 17.14 (116) – 11.7 (73) | Essendon | SCG | Sydney by 43 |
| 2006 1 Apr | Round 1 | Essendon | 17.6 (108) – 12.9 (81) | Sydney | Marvel Stadium | Essendon by 27 |
| 2005 6 Aug | Round 19 | Essendon | 15.8 (98) – 18.10 (118) | Sydney | Marvel Stadium | Sydney by 20 |
| 2005 7 May | Round 7 | Sydney | 13.16 (94) – 14.4 (88) | Essendon | Stadium Australia | Sydney by 6 |
| 2004 21 Aug | Round 21 | Sydney | 17.8 (110) – 12.18 (90) | Essendon | Stadium Australia | Sydney by 20 |
| 2004 1 May | Round 6 | Essendon | 16.12 (108) – 15.8 (98) | Sydney | MCG | Essendon by 10 |
| 2003 7 June | Round 11 | Sydney | 21.7 (133) – 12.7 (79) | Essendon | Stadium Australia | Sydney by 54 |
| 2002 25 May | Round 9 | Sydney | 11.17 (83) – 12.13 (85) | Essendon | Stadium Australia | Essendon by 2 |
| 2001 12 Aug | Round 19 | Essendon | 11.13 (79) – 11.11 (77) | Sydney | Marvel Stadium | Essendon by 2 |
| 2001 20 Apr | Round 4 | Sydney | 6.19 (55) – 15.12 (102) | Essendon | SCG | Essendon by 47 |
| 2000 11 June | Round 14 | Sydney | 11.10 (76) – 12.17 (89) | Essendon | SCG | Essendon by 13 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1999 5 Sept | Finals Week 1 | Essendon | 18.15 (123) – 7.12 (54) | Sydney | MCG | Essendon by 69 |
| 1999 31 July | Round 18 | Sydney | 11.13 (79) – 15.3 (93) | Essendon | SCG | Essendon by 14 |
| 1999 10 Apr | Round 3 | Essendon | 22.17 (149) – 9.14 (68) | Sydney | MCG | Essendon by 81 |
| 1998 5 June | Round 11 | Essendon | 24.16 (160) – 15.10 (100) | Sydney | MCG | Essendon by 60 |
| 1997 13 July | Round 15 | Sydney | 11.13 (79) – 11.12 (78) | Essendon | SCG | Sydney by 1 |
| 1996 21 Sept | Preliminary Finals | Sydney | 10.10 (70) – 10.9 (69) | Essendon | SCG | Sydney by 1 |
| 1996 24 Aug | Round 21 | Essendon | 14.16 (100) – 12.10 (82) | Sydney | MCG | Essendon by 18 |
| 1996 3 May | Round 6 | Sydney | 14.6 (90) – 12.18 (90) | Essendon | SCG | Draw |
| 1995 2 July | Round 13 | Sydney | 21.12 (138) – 17.17 (119) | Essendon | SCG | Sydney by 19 |
| 1994 26 June | Round 14 | Essendon | 19.15 (129) – 14.11 (95) | Sydney | MCG | Essendon by 34 |
| 1993 6 Aug | Round 19 | Essendon | 18.9 (117) – 13.18 (96) | Sydney | MCG | Essendon by 21 |
| 1993 18 Apr | Round 4 | Sydney | 14.11 (95) – 28.13 (181) | Essendon | SCG | Essendon by 86 |
| 1992 31 May | Round 11 | Essendon | 16.20 (116) – 10.13 (73) | Sydney | MCG | Essendon by 43 |
| 1991 3 Aug | Round 20 | Essendon | 22.19 (151) – 12.12 (84) | Sydney | Windy Hill | Essendon by 67 |
| 1991 19 Apr | Round 5 | Sydney | 19.16 (130) – 24.17 (161) | Essendon | SCG | Essendon by 31 |
| 1990 3 June | Round 10 | Sydney | 11.8 (74) – 25.14 (164) | Essendon | SCG | Essendon by 90 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1989 25 Aug | Round 21 | Sydney | 15.20 (110) – 15.14 (104) | Essendon | SCG | Sydney by 6 |
| 1989 17 June | Round 12 | Essendon | 7.8 (50) – 7.13 (55) | Sydney | Windy Hill | Sydney by 5 |
| 1988 3 June | Round 10 | Sydney | 11.11 (77) – 8.7 (55) | Essendon | SCG | Sydney by 22 |
| 1987 26 July | Round 17 | Sydney | 36.20 (236) – 11.7 (73) | Essendon | SCG | Sydney by 163 |
| 1987 20 Apr | Round 4 | Essendon | 17.11 (113) – 9.12 (66) | Sydney | Windy Hill | Essendon by 47 |
| 1986 13 July | Round 16 | Sydney | 24.18 (162) – 15.13 (103) | Essendon | SCG | Sydney by 59 |
| 1986 9 June | Round 11 | Essendon | 9.4 (58) – 10.18 (78) | Sydney | Windy Hill | Sydney by 20 |
| 1985 1 Sept | Round 22 | Sydney | 11.12 (78) – 24.21 (165) | Essendon | SCG | Essendon by 87 |
| 1985 8 June | Round 11 | Essendon | 17.11 (113) – 11.5 (71) | Sydney | Windy Hill | Essendon by 42 |
| 1984 26 Aug | Round 21 | Sydney | 23.17 (155) – 14.15 (99) | Essendon | SCG | Sydney by 56 |
| 1984 9 June | Round 11 | Essendon | 20.15 (135) – 14.10 (94) | Sydney | Windy Hill | Essendon by 41 |
| 1983 11 June | Round 12 | Essendon | 23.18 (156) – 13.5 (83) | Sydney | Windy Hill | Essendon by 73 |
| 1983 27 Mar | Round 1 | Sydney | 17.9 (111) – 15.20 (110) | Essendon | SCG | Sydney by 1 |
| 1982 17 July | Round 16 | Essendon | 12.10 (82) – 17.13 (115) | Sydney | Windy Hill | Sydney by 33 |
| 1982 2 May | Round 6 | Sydney | 15.21 (111) – 18.9 (117) | Essendon | SCG | Essendon by 6 |
| 1981 22 Aug | Round 21 | Essendon | 26.23 (179) – 10.8 (68) | Sydney | Windy Hill | Essendon by 111 |
| 1981 8 June | Round 11 | Sydney | 12.8 (80) – 15.18 (108) | Essendon | Lake Oval | Essendon by 28 |
| 1980 19 July | Round 16 | Essendon | 20.9 (129) – 19.19 (133) | Sydney | Windy Hill | Sydney by 4 |
| 1980 12 Apr | Round 3 | Sydney | 14.17 (101) – 24.12 (156) | Essendon | Waverley Park | Essendon by 55 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1979 25 Aug | Round 21 | Sydney | 10.16 (76) – 13.17 (95) | Essendon | Waverley Park | Essendon by 19 |
| 1979 9 June | Round 10 | Essendon | 16.19 (115) – 14.15 (99) | Sydney | Windy Hill | Essendon by 16 |
| 1978 24 June | Round 12 | Sydney | 13.19 (97) – 17.18 (120) | Essendon | Lake Oval | Essendon by 23 |
| 1978 1 Apr | Round 1 | Essendon | 19.9 (123) – 14.18 (102) | Sydney | Windy Hill | Essendon by 21 |
| 1977 25 June | Round 13 | Essendon | 9.9 (63) – 6.15 (51) | Sydney | Windy Hill | Essendon by 12 |
| 1977 9 Apr | Round 2 | Sydney | 27.13 (175) – 15.8 (98) | Essendon | Lake Oval | Sydney by 77 |
| 1976 3 July | Round 14 | Essendon | 13.15 (93) – 12.6 (78) | Sydney | Windy Hill | Essendon by 15 |
| 1976 24 Apr | Round 4 | Sydney | 22.11 (143) – 16.13 (109) | Essendon | Lake Oval | Sydney by 34 |
| 1975 28 June | Round 13 | Essendon | 19.18 (132) – 17.12 (114) | Sydney | Windy Hill | Essendon by 18 |
| 1975 12 Apr | Round 2 | Sydney | 15.12 (102) – 19.17 (131) | Essendon | Lake Oval | Essendon by 29 |
| 1974 29 June | Round 13 | Sydney | 11.16 (82) – 14.12 (96) | Essendon | Lake Oval | Essendon by 14 |
| 1974 15 Apr | Round 2 | Essendon | 21.24 (150) – 10.18 (78) | Sydney | Windy Hill | Essendon by 72 |
| 1973 30 June | Round 13 | Essendon | 20.19 (139) – 16.14 (110) | Sydney | Windy Hill | Essendon by 29 |
| 1973 14 Apr | Round 2 | Sydney | 15.19 (109) – 21.20 (146) | Essendon | Lake Oval | Essendon by 37 |
| 1972 1 July | Round 13 | Sydney | 12.12 (84) – 13.9 (87) | Essendon | Lake Oval | Essendon by 3 |
| 1972 8 Apr | Round 2 | Essendon | 16.11 (107) – 7.18 (60) | Sydney | Windy Hill | Essendon by 47 |
| 1971 31 July | Round 18 | Sydney | 13.8 (86) – 13.18 (96) | Essendon | Lake Oval | Essendon by 10 |
| 1971 15 May | Round 7 | Essendon | 12.17 (89) – 16.9 (105) | Sydney | Windy Hill | Sydney by 16 |
| 1970 4 July | Round 14 | Essendon | 5.10 (40) – 11.5 (71) | Sydney | Waverley Park | Sydney by 31 |
| 1970 18 Apr | Round 3 | Sydney | 12.17 (89) – 15.10 (100) | Essendon | Lake Oval | Essendon by 11 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1969 14 June | Round 10 | Sydney | 15.13 (103) – 18.15 (123) | Essendon | Lake Oval | Essendon by 20 |
| 1968 27 July | Round 15 | Sydney | 7.12 (54) – 14.13 (97) | Essendon | Lake Oval | Essendon by 43 |
| 1968 4 May | Round 4 | Essendon | 16.19 (115) – 10.15 (75) | Sydney | Windy Hill | Essendon by 40 |
| 1967 5 Aug | Round 15 | Essendon | 14.15 (99) – 7.16 (58) | Sydney | Windy Hill | Essendon by 41 |
| 1967 6 May | Round 4 | Sydney | 18.19 (127) – 13.10 (88) | Essendon | Lake Oval | Sydney by 39 |
| 1966 9 July | Round 11 | Sydney | 12.10 (82) – 13.12 (90) | Essendon | Lake Oval | Essendon by 8 |
| 1965 21 Aug | Round 17 | Essendon | 14.13 (97) – 4.7 (31) | Sydney | Windy Hill | Essendon by 66 |
| 1965 22 May | Round 6 | Sydney | 14.12 (96) – 12.16 (88) | Essendon | Lake Oval | Sydney by 8 |
| 1964 22 Aug | Round 18 | Essendon | 28.16 (184) – 2.7 (19) | Sydney | Windy Hill | Essendon by 165 |
| 1964 30 May | Round 7 | Sydney | 11.18 (84) – 14.12 (96) | Essendon | Lake Oval | Essendon by 12 |
| 1963 20 July | Round 11 | Sydney | 6.10 (46) – 12.20 (92) | Essendon | Lake Oval | Essendon by 46 |
| 1962 25 Aug | Round 18 | Essendon | 13.15 (93) – 13.10 (88) | Sydney | Windy Hill | Essendon by 5 |
| 1962 2 June | Round 7 | Sydney | 7.11 (53) – 16.15 (111) | Essendon | Lake Oval | Essendon by 58 |
| 1961 19 Aug | Round 17 | Sydney | 11.12 (78) – 16.11 (107) | Essendon | Lake Oval | Essendon by 29 |
| 1961 20 May | Round 6 | Essendon | 20.13 (133) – 6.18 (54) | Sydney | Windy Hill | Essendon by 79 |
| 1960 18 June | Round 9 | Essendon | 13.10 (88) – 12.15 (87) | Sydney | Windy Hill | Essendon by 1 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1959 1 Aug | Round 14 | Essendon | 10.19 (79) – 8.14 (62) | Sydney | Windy Hill | Essendon by 17 |
| 1959 9 May | Round 3 | Sydney | 9.11 (65) – 7.10 (52) | Essendon | Lake Oval | Sydney by 13 |
| 1958 21 June | Round 11 | Sydney | 8.13 (61) – 15.13 (103) | Essendon | Lake Oval | Essendon by 42 |
| 1957 10 Aug | Round 16 | Essendon | 10.15 (75) – 7.13 (55) | Sydney | Windy Hill | Essendon by 20 |
| 1957 18 May | Round 5 | Sydney | 7.16 (58) – 14.16 (100) | Essendon | Lake Oval | Essendon by 42 |
| 1956 11 Aug | Round 17 | Essendon | 11.10 (76) – 7.16 (58) | Sydney | Windy Hill | Essendon by 18 |
| 1956 19 May | Round 6 | Sydney | 15.8 (98) – 11.20 (86) | Essendon | Lake Oval | Sydney by 12 |
| 1955 4 June | Round 8 | Essendon | 13.14 (92) – 7.12 (54) | Sydney | Windy Hill | Essendon by 38 |
| 1954 24 July | Round 13 | Sydney | 8.18 (66) – 13.8 (86) | Essendon | Lake Oval | Essendon by 20 |
| 1954 24 Apr | Round 2 | Essendon | 5.18 (48) – 8.13 (61) | Sydney | Windy Hill | Sydney by 13 |
| 1953 25 July | Round 13 | Essendon | 12.11 (83) – 8.14 (62) | Sydney | Windy Hill | Essendon by 21 |
| 1953 2 May | Round 2 | Sydney | 13.21 (99) – 13.11 (89) | Essendon | Lake Oval | Sydney by 10 |
| 1952 12 July | Round 12 | Sydney | 8.12 (60) – 9.15 (69) | Essendon | Lake Oval | Essendon by 9 |
| 1951 4 Aug | Round 14 | Essendon | 16.10 (106) – 8.12 (60) | Sydney | Windy Hill | Essendon by 46 |
| 1951 5 May | Round 3 | Sydney | 14.20 (104) – 14.7 (91) | Essendon | Lake Oval | Sydney by 13 |
| 1950 15 July | Round 13 | Sydney | 8.9 (57) – 22.17 (149) | Essendon | Lake Oval | Essendon by 92 |
| 1950 29 Apr | Round 2 | Essendon | 29.7 (181) – 10.16 (76) | Sydney | Windy Hill | Essendon by 105 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1949 11 June | Round 9 | Sydney | 15.16 (106) – 12.9 (81) | Essendon | Lake Oval | Sydney by 25 |
| 1948 7 Aug | Round 15 | Essendon | 11.21 (87) – 8.11 (59) | Sydney | Windy Hill | Essendon by 28 |
| 1948 8 May | Round 4 | Sydney | 11.12 (78) – 20.20 (140) | Essendon | Lake Oval | Essendon by 62 |
| 1947 5 July | Round 12 | Sydney | 8.14 (62) – 11.17 (83) | Essendon | Lake Oval | Essendon by 21 |
| 1947 19 Apr | Round 1 | Essendon | 16.23 (119) – 10.8 (68) | Sydney | Windy Hill | Essendon by 51 |
| 1946 20 July | Round 13 | Sydney | 9.13 (67) – 10.8 (68) | Essendon | Junction Oval | Essendon by 1 |
| 1946 27 Apr | Round 2 | Essendon | 10.11 (71) – 8.5 (53) | Sydney | Windy Hill | Essendon by 18 |
| 1945 23 June | Round 10 | Sydney | 12.15 (87) – 5.11 (41) | Essendon | Junction Oval | Sydney by 46 |
| 1944 2 Sept | Round 18 | Essendon | 17.24 (126) – 6.8 (44) | Sydney | Windy Hill | Essendon by 82 |
| 1944 15 July | Round 11 | Sydney | 7.15 (57) – 15.16 (106) | Essendon | Junction Oval | Essendon by 49 |
| 1943 8 May | Round 1 | Essendon | 18.9 (117) – 13.14 (92) | Sydney | Windy Hill | Essendon by 25 |
| 1942 12 Sept | Preliminary Finals | Essendon | 19.10 (124) – 14.12 (96) | Sydney | Princes Park | Essendon by 28 |
| 1942 18 July | Round 11 | Essendon | 10.15 (75) – 8.7 (55) | Sydney | Windy Hill | Essendon by 20 |
| 1941 23 Aug | Round 17 | Essendon | 12.23 (95) – 7.4 (46) | Sydney | Windy Hill | Essendon by 49 |
| 1941 7 June | Round 6 | Sydney | 8.13 (61) – 13.18 (96) | Essendon | Lake Oval | Essendon by 35 |
| 1940 27 July | Round 14 | Sydney | 9.6 (60) – 7.16 (58) | Essendon | Lake Oval | Sydney by 2 |
| 1940 11 May | Round 3 | Essendon | 12.14 (86) – 10.15 (75) | Sydney | Windy Hill | Essendon by 11 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1939 12 June | Round 8 | Essendon | 9.16 (70) – 13.13 (91) | Sydney | Windy Hill | Sydney by 21 |
| 1938 13 Aug | Round 16 | Sydney | 13.13 (91) – 12.14 (86) | Essendon | Lake Oval | Sydney by 5 |
| 1938 21 May | Round 5 | Essendon | 15.15 (105) – 11.19 (85) | Sydney | Windy Hill | Essendon by 20 |
| 1937 28 Aug | Round 18 | Sydney | 10.16 (76) – 11.7 (73) | Essendon | Lake Oval | Sydney by 3 |
| 1937 5 June | Round 7 | Essendon | 16.12 (108) – 11.10 (76) | Sydney | Windy Hill | Essendon by 32 |
| 1936 22 Aug | Round 16 | Essendon | 12.16 (88) – 11.30 (96) | Sydney | Windy Hill | Sydney by 8 |
| 1936 30 May | Round 5 | Sydney | 15.21 (111) – 11.13 (79) | Essendon | Lake Oval | Sydney by 32 |
| 1935 22 June | Round 9 | Sydney | 13.22 (100) – 9.7 (61) | Essendon | Lake Oval | Sydney by 39 |
| 1934 18 Aug | Round 14 | Essendon | 9.17 (71) – 22.14 (146) | Sydney | Windy Hill | Sydney by 75 |
| 1934 19 May | Round 3 | Sydney | 23.10 (148) – 15.16 (106) | Essendon | Lake Oval | Sydney by 42 |
| 1933 19 Aug | Round 16 | Sydney | 11.16 (82) – 6.4 (40) | Essendon | Lake Oval | Sydney by 42 |
| 1933 27 May | Round 5 | Essendon | 12.11 (83) – 17.15 (117) | Sydney | Windy Hill | Sydney by 34 |
| 1932 20 Aug | Round 16 | Essendon | 13.12 (90) – 11.20 (86) | Sydney | Windy Hill | Essendon by 4 |
| 1932 28 May | Round 5 | Sydney | 14.15 (99) – 9.11 (65) | Essendon | Lake Oval | Sydney by 34 |
| 1931 4 July | Round 9 | Sydney | 10.13 (73) – 9.9 (63) | Essendon | Lake Oval | Sydney by 10 |
| 1930 19 July | Round 12 | Essendon | 15.16 (106) – 16.12 (108) | Sydney | Windy Hill | Sydney by 2 |
| 1930 31 May | Round 5 | Sydney | 6.15 (51) – 15.14 (104) | Essendon | Lake Oval | Essendon by 53 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1929 17 Aug | Round 16 | Sydney | 14.10 (94) – 13.10 (88) | Essendon | Lake Oval | Sydney by 6 |
| 1929 25 May | Round 5 | Essendon | 10.18 (78) – 7.10 (52) | Sydney | Windy Hill | Essendon by 26 |
| 1928 28 July | Round 14 | Sydney | 11.17 (83) – 18.11 (119) | Essendon | Lake Oval | Essendon by 36 |
| 1928 5 May | Round 3 | Essendon | 12.13 (85) – 5.11 (41) | Sydney | Windy Hill | Essendon by 44 |
| 1927 25 June | Round 9 | Essendon | 12.12 (84) – 15.9 (99) | Sydney | Windy Hill | Sydney by 15 |
| 1926 11 Sept | Round 18 | Essendon | 9.17 (71) – 10.14 (74) | Sydney | Windy Hill | Sydney by 3 |
| 1926 26 June | Round 9 | Sydney | 9.15 (69) – 8.9 (57) | Essendon | Lake Oval | Sydney by 12 |
| 1925 13 June | Round 7 | Essendon | 9.11 (65) – 8.9 (57) | Sydney | Windy Hill | Essendon by 8 |
| 1924 20 Sept | Semi-Finals | Essendon | 10.12 (72) – 4.15 (39) | Sydney | MCG | Essendon by 33 |
| 1924 12 July | Round 12 | Sydney | 9.8 (62) – 6.13 (49) | Essendon | Lake Oval | Sydney by 13 |
| 1924 10 May | Round 3 | Essendon | 12.13 (85) – 8.11 (59) | Sydney | Windy Hill | Essendon by 26 |
| 1923 29 Sept | Semi-Finals | Sydney | 10.14 (74) – 8.9 (57) | Essendon | MCG | Sydney by 17 |
| 1923 28 July | Round 12 | Essendon | 10.8 (68) – 7.9 (51) | Sydney | Windy Hill | Essendon by 17 |
| 1923 19 May | Round 3 | Sydney | 4.15 (39) – 6.13 (49) | Essendon | Lake Oval | Essendon by 10 |
| 1922 29 July | Round 12 | Sydney | 14.15 (99) – 11.8 (74) | Essendon | Lake Oval | Sydney by 25 |
| 1922 20 May | Round 3 | Essendon | 12.12 (84) – 8.13 (61) | Sydney | Windy Hill | Essendon by 23 |
| 1921 23 July | Round 12 | Essendon | 8.13 (61) – 5.13 (43) | Sydney | East Melbourne | Essendon by 18 |
| 1921 21 May | Round 3 | Sydney | 4.14 (38) – 11.15 (81) | Essendon | Lake Oval | Essendon by 43 |
| 1920 17 July | Round 12 | Sydney | 8.14 (62) – 7.7 (49) | Essendon | Lake Oval | Sydney by 13 |
| 1920 15 May | Round 3 | Essendon | 7.13 (55) – 9.9 (63) | Sydney | East Melbourne | Sydney by 8 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1919 16 Aug | Round 14 | Sydney | 12.15 (87) – 8.7 (55) | Essendon | Lake Oval | Sydney by 32 |
| 1919 31 May | Round 5 | Essendon | 7.8 (50) – 9.16 (70) | Sydney | East Melbourne | Sydney by 20 |
| 1918 3 Aug | Round 13 | Sydney | 12.13 (85) – 7.10 (52) | Essendon | Lake Oval | Sydney by 33 |
| 1918 15 June | Round 6 | Essendon | 4.8 (32) – 7.10 (52) | Sydney | East Melbourne | Sydney by 20 |
| 1915 31 July | Round 15 | Sydney | 13.19 (97) – 6.4 (40) | Essendon | Lake Oval | Sydney by 57 |
| 1915 29 May | Round 6 | Essendon | 8.7 (55) – 8.16 (64) | Sydney | East Melbourne | Sydney by 9 |
| 1914 25 July | Round 15 | Sydney | 4.8 (32) – 15.14 (104) | Essendon | Lake Oval | Essendon by 72 |
| 1914 30 May | Round 6 | Essendon | 5.11 (41) – 5.13 (43) | Sydney | East Melbourne | Sydney by 2 |
| 1913 19 July | Round 13 | Sydney | 5.12 (42) – 7.20 (62) | Essendon | Lake Oval | Essendon by 20 |
| 1913 17 May | Round 4 | Essendon | 7.14 (56) – 15.13 (103) | Sydney | East Melbourne | Sydney by 47 |
| 1912 28 Sept | Grand Final | Essendon | 5.17 (47) – 4.9 (33) | Sydney | MCG | Essendon by 14 |
| 1912 14 Sept | Semi-Finals | Essendon | 7.12 (54) – 6.6 (42) | Sydney | MCG | Essendon by 12 |
| 1912 20 July | Round 13 | Essendon | 7.10 (52) – 9.11 (65) | Sydney | East Melbourne | Sydney by 13 |
| 1912 18 May | Round 4 | Sydney | 8.8 (56) – 9.8 (62) | Essendon | Lake Oval | Essendon by 6 |
| 1911 2 Sept | Round 18 | Essendon | 9.9 (63) – 8.10 (58) | Sydney | East Melbourne | Essendon by 5 |
| 1911 17 June | Round 9 | Sydney | 6.8 (44) – 5.11 (41) | Essendon | Lake Oval | Sydney by 3 |
| 1910 16 July | Round 12 | Essendon | 6.9 (45) – 5.4 (34) | Sydney | East Melbourne | Essendon by 11 |
| 1910 21 May | Round 3 | Sydney | 10.7 (67) – 11.7 (73) | Essendon | Lake Oval | Essendon by 6 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1909 21 Aug | Round 16 | Sydney | 6.5 (41) – 5.7 (37) | Essendon | Lake Oval | Sydney by 4 |
| 1909 7 June | Round 7 | Essendon | 9.8 (62) – 9.9 (63) | Sydney | East Melbourne | Sydney by 1 |
| 1908 15 Aug | Round 17 | Sydney | 5.8 (38) – 3.14 (32) | Essendon | Lake Oval | Sydney by 6 |
| 1908 13 June | Round 8 | Essendon | 8.11 (59) – 6.9 (45) | Sydney | East Melbourne | Essendon by 14 |
| 1907 31 Aug | Round 17 | Essendon | 6.7 (43) – 15.9 (99) | Sydney | East Melbourne | Sydney by 56 |
| 1907 13 July | Round 11 | Sydney | 8.11 (59) – 6.11 (47) | Essendon | Lake Oval | Sydney by 12 |
| 1907 18 May | Round 4 | Essendon | 6.8 (44) – 6.11 (47) | Sydney | East Melbourne | Sydney by 3 |
| 1906 1 Sept | Round 16 | Essendon | 3.13 (31) – 10.6 (66) | Sydney | East Melbourne | Sydney by 35 |
| 1906 30 June | Round 8 | Sydney | 3.8 (26) – 8.11 (59) | Essendon | Lake Oval | Essendon by 33 |
| 1906 5 May | Round 1 | Essendon | 8.12 (60) – 9.13 (67) | Sydney | East Melbourne | Sydney by 7 |
| 1905 22 July | Round 11 | Sydney | 7.8 (50) – 6.13 (49) | Essendon | Lake Oval | Sydney by 1 |
| 1905 27 May | Round 4 | Essendon | 14.11 (95) – 5.9 (39) | Sydney | East Melbourne | Essendon by 56 |
| 1904 27 Aug | Round 16 | Sydney | 4.3 (27) – 8.11 (59) | Essendon | Lake Oval | Essendon by 32 |
| 1904 25 June | Round 8 | Sydney | 10.9 (69) – 4.5 (29) | Essendon | Lake Oval | Sydney by 40 |
| 1904 7 May | Round 1 | Essendon | 8.10 (58) – 2.5 (17) | Sydney | East Melbourne | Essendon by 41 |
| 1903 29 Aug | Round 17 | Essendon | 14.10 (94) – 5.7 (37) | Sydney | East Melbourne | Essendon by 57 |
| 1903 25 July | Round 13 | Sydney | 5.7 (37) – 7.17 (59) | Essendon | Lake Oval | Essendon by 22 |
| 1903 6 June | Round 6 | Essendon | 5.11 (41) – 6.12 (48) | Sydney | East Melbourne | Sydney by 7 |
| 1902 12 July | Round 11 | Sydney | 5.6 (36) – 6.7 (43) | Essendon | Lake Oval | Essendon by 7 |
| 1902 24 May | Round 4 | Essendon | 5.8 (38) – 4.11 (35) | Sydney | East Melbourne | Essendon by 3 |
| 1901 10 Aug | Round 15 | Sydney | 1.3 (9) – 10.9 (69) | Essendon | Lake Oval | Essendon by 60 |
| 1901 20 July | Round 13 | Essendon | 6.16 (52) – 8.3 (51) | Sydney | East Melbourne | Essendon by 1 |
| 1901 1 June | Round 6 | Sydney | 5.5 (35) – 3.23 (41) | Essendon | Lake Oval | Essendon by 6 |
| 1900 25 Aug | Round 15 | Sydney | 3.1 (19) – 9.5 (59) | Essendon | Lake Oval | Essendon by 40 |
| 1900 23 June | Round 8 | Sydney | 4.14 (38) – 1.4 (10) | Essendon | Lake Oval | Sydney by 28 |
| 1900 5 May | Round 1 | Essendon | 12.10 (82) – 4.2 (26) | Sydney | East Melbourne | Essendon by 56 |
| Year | Round | Home | Score | Away | Venue | Result |
|---|---|---|---|---|---|---|
| 1899 9 Sept | Round 17 | Sydney | 3.10 (28) – 2.1 (13) | Essendon | Lake Oval | Sydney by 15 |
| 1899 15 July | Round 10 | Sydney | 5.5 (35) – 7.9 (51) | Essendon | Lake Oval | Essendon by 16 |
| 1899 24 May | Round 3 | Essendon | 1.9 (15) – 0.9 (9) | Sydney | East Melbourne | Essendon by 6 |
| 1898 3 Sept | Round 16 | Sydney | 3.6 (24) – 5.11 (41) | Essendon | Lake Oval | Essendon by 17 |
| 1898 9 July | Round 9 | Essendon | 7.12 (54) – 4.6 (30) | Sydney | East Melbourne | Essendon by 24 |
| 1898 21 May | Round 2 | Sydney | 3.9 (27) – 5.8 (38) | Essendon | Lake Oval | Essendon by 11 |
| 1897 31 July | Round 13 | Essendon | 8.1 (49) – 6.9 (45) | Sydney | East Melbourne | Essendon by 4 |
| 1897 19 June | Round 6 | Sydney | 2.4 (16) – 1.13 (19) | Essendon | Lake Oval | Essendon by 3 |
Includes every completed VFL/AFL game between the two clubs, home-and-away and finals.