| Year | Coach | Captain | W. S. Crichton Medal | Leading goalkicker |
| 1897 # | — | George Stuckey | — | Norman Waugh (23) |
| 1898 | — | Stuckey, GeorgeGeorge Stuckey | — | Moore, CharlieCharlie Moore (20) |
| 1899 | — | Stuckey, GeorgeGeorge Stuckey | — | Cleghorn, ArthurArthur Cleghorn (15) |
| 1900 | — | Stuckey, GeorgeGeorge Stuckey | — | Thurgood, AlbertAlbert Thurgood (25) |
| 1901 # | — | Collins, TodTod Collins | Thurgood, AlbertAlbert Thurgood | Hiskins, FredFred Hiskins (34) |
| 1902 | — | Collins, TodTod Collins | — | Thurgood, AlbertAlbert Thurgood (32) |
| 1903 | — | Anderson, JimJim Anderson | Gavin, HughHugh Gavin | Madden, MickMick Madden (15) |
| 1904 | — | Anderson, JimJim Anderson / Gavin, HughHugh Gavin | — | Madden, MickMick Madden (25) |
| 1905 | — | Robinson, WilliamWilliam Robinson | — | Barker, GeorgeGeorge Barker (29) |
| 1906 | — | McKenzie, JackJack McKenzie | McKenzie, JackJack McKenzie | Yeo, NormanNorman Yeo (31) |
| 1907 | — | Griffith, WilliamWilliam Griffith | — | Martin, JimJim Martin (16) |
| 1908 | Smith, DaveDave Smith | Griffith, WilliamWilliam Griffith | Busbridge, BillBill Busbridge | Smith, DaveDave Smith (26) |
| 1909 | Smith, DaveDave Smith | Griffith, WilliamWilliam Griffith | Busbridge, BillBill Busbridge | Shea, PaddyPaddy Shea (40) |
| 1910 | Belcher, AlanAlan Belcher | Belcher, AlanAlan Belcher | — | Armstrong, BertBert Armstrong (40) |
| 1911 # | Worrall, JackJack Worrall | Smith, DaveDave Smith | Cameron, ErnestErnest Cameron | Armstrong, LouLou Armstrong (35) |
| 1912 # | Worrall, JackJack Worrall | Belcher, AlanAlan Belcher | Cameron, ErnestErnest Cameron | Kirby, JackJack Kirby (43) |
| 1913 | Worrall, JackJack Worrall | Belcher, AlanAlan Belcher | Baring, FredFred Baring | Kirby, JackJack Kirby (29) |
| 1914 | Worrall, JackJack Worrall | Belcher, AlanAlan Belcher | — | Lumsden, ErnieErnie Lumsden (28) |
| 1915 | Worrall, JackJack Worrall | Belcher, AlanAlan Belcher | — | Walker, BillBill Walker (14) |
| 1916 | — | — | — | — |
| 1917 | — | — | — | — |
| 1918 | Worrall, JackJack Worrall | Baring, FredFred Baring | — | Hall, NormNorm Hall (15) |
| 1919 | Worrall, JackJack Worrall | Belcher, AlanAlan Belcher | — | Walsh, DaveDave Walsh (15) |
| 1920 | Ogden, PercyPercy Ogden | Ogden, PercyPercy Ogden | Garden, JockJock Garden | McDonald, FrankFrank McDonald (33) |
| 1921 | Ogden, PercyPercy Ogden | Ogden, PercyPercy Ogden | — | McDonald, FrankFrank McDonald (17) |
| 1922 | Gravenall, SamSam Gravenall | Barker, SidSid Barker | Fitzmaurice, TomTom Fitzmaurice | Moriarty, JackJack Moriarty (36) |
| 1923 # | Barker, SidSid Barker | Barker, SidSid Barker | Fitzmaurice, TomTom Fitzmaurice | Greg Stockdale (68) |
| 1924 # | Barker, SidSid Barker | Barker, SidSid Barker | Fitzmaurice, TomTom Fitzmaurice | Jenkins, TommyTommy Jenkins (50) |
| 1925 | Maher, FredFred Maher | Maher, FrankFrank Maher | Stockdale, GregGreg Stockdale | Jenkins, TommyTommy Jenkins (37) |
| 1926 | Maher, FredFred Maher | Maher, FrankFrank Maher | Joe Harrison | Greg Stockdale (36) |
| 1927 | Maher, FredFred Maher | Maher, FrankFrank Maher | Maher, FrankFrank Maher | Vosti, JackJack Vosti (35) |
| 1928 | Hardy, CharlieCharlie Hardy | Maher, FrankFrank Maher | Norm Beckton | Greg Stockdale (39) |
| 1929 | Hardy, CharlieCharlie Hardy | Beckton, NormNorm Beckton | Okey, HowardHoward Okey | Forbes, KeithKeith Forbes / Johnson, LenLen Johnson (40) |
| 1930 | Hardy, CharlieCharlie Hardy | Beckton, NormNorm Beckton | Forbes, KeithKeith Forbes | Forbes, KeithKeith Forbes (54) |
| 1931 | Garnet Campbell | Garnet Campbell | Tom Clarke | Ted Freyer (50) |
| 1932 | Garnet Campbell | Garnet Campbell | Syd Carman | Ted Freyer (52) |
| 1933 | Garnet Campbell | Garnet Campbell | Paddy Walsh | Ted Freyer (51) |
| 1934 | Charlie May | Keith Forbes | Dick Reynolds * | Ted Freyer (61) |
| 1935 | Charlie May | Keith Forbes | Keith Forbes | Keith Forbes (52) |
| 1936 | Jack Baggott | Jack Baggott | Dick Reynolds | Ted Freyer (50) |
| 1937 | Jack Baggott | Jack Baggott / Keith Forbes | Dick Reynolds * | Keith Forbes (44) |
| 1938 | Jack Baggott | Len Webster | Dick Reynolds * | Tom Reynolds (68) |
| 1939 | Jack Baggott / Harry Hunter / Dick Reynolds | Dick Reynolds | Dick Reynolds | Tom Reynolds (71) |
| 1940 | Dick Reynolds | Dick Reynolds | Hugh Torney | Ted Bryce (48) |
| 1941 | Dick Reynolds | Dick Reynolds | Wally Buttsworth | Tom Reynolds (65) |
| 1942 # | Dick Reynolds | Dick Reynolds | Dick Reynolds | Tom Reynolds (61) |
| 1943 | Dick Reynolds | Dick Reynolds | Dick Reynolds | Dick Reynolds (31) |
| 1944 | Dick Reynolds | Dick Reynolds | Percy Bushby | Ray Powell (42) |
| 1945 | Dick Reynolds | Dick Reynolds | Wally Buttsworth | Bill Brittingham (48) |
| 1946 # | Dick Reynolds | Dick Reynolds | Bill Hutchison | Bill Brittingham (66) |
| 1947 | Dick Reynolds | Dick Reynolds | Wally Buttsworth | Ted Leehane (50) |
| 1948 | Dick Reynolds | Dick Reynolds | Bill Hutchison | Bill Hutchison (52) |
| 1949 # | Dick Reynolds | Dick Reynolds | John Coleman | John Coleman (100) |
| 1950 # | Dick Reynolds | Dick Reynolds | Bill Hutchison | John Coleman (120) |
| 1951 | Dick Reynolds | Bill Hutchison | Norm McDonald | John Coleman (75) |
| 1952 | Dick Reynolds | Bill Hutchison | Bill Hutchison * | John Coleman (103) |
| 1953 | Dick Reynolds | Bill Hutchison | Bill Hutchison * | John Coleman (97) |
| 1954 | Dick Reynolds | Bill Hutchison | John Gill | John Coleman (42) |
| 1955 | Dick Reynolds | Bill Hutchison | Bill Hutchison | Hugh Mitchell (51) |
| 1956 | Dick Reynolds | Bill Hutchison | Bill Hutchison | Graham Willey (33) |
| 1957 | Dick Reynolds | Bill Hutchison | Reg Burgess | Fred Gallagher (34) |
| 1958 | Dick Reynolds | Jack Clarke | Jack Clarke | John Birt (31) |
| 1958 | Dick Reynolds | Jack Clarke | Jack Clarke | John Birt (31) |
| 1959 | Dick Reynolds | Jack Clarke | Hugh Mitchell | Ron Evans (78 |
| 1960 | Dick Reynolds | Jack Clarke | Reg Burgess | Ron Evans (67) |
| 1961 | John Coleman | Jack Clarke | John Birt | Hugh Mitchell (33) |
| 1962 # | John Coleman | Jack Clarke | Jack Clarke | Charlie Payne (39) |
| 1963 | John Coleman | Jack Clarke | Ken Fraser | Charlie Payne (36) |
| 1964 | John Coleman | Jack Clarke | Ken Fraser | Hugh Mitchell (32) |
| 1965 # | John Coleman | Ken Fraser | John Birt | Ted Fordham (54) |
| 1966 | John Coleman | Ken Fraser | Don McKenzie | Ted Fordham (76) |
| 1967 | John Coleman | Ken Fraser | John Birt | Alan Noonan (40) |
| 1968 | Jack Clarke | Ken Fraser | Barry Davis | Alan Noonan (51) |
| 1969 | Jack Clarke | Don McKenzie | Barry Davis | Alan Noonan (43) |
| 1970 | Jack Clarke | Barry Davis | Darryl Gerlach | Geoff Blethyn (33) |
| 1971 | John Birt | Barry Davis | Barry Davis | Alan Noonan (31) |
| 1972 | Des Tuddenham | Des Tuddenham | Neville Fields | Geoff Blethyn (107) |
| 1973 | Des Tuddenham | Des Tuddenham | Andy Wilson | Alan Noonan (63) |
| 1974 | Des Tuddenham | Des Tuddenham | Graham Moss | Alan Noonan (77) |
| 1975 | Des Tuddenham | Des Tuddenham | Graham Moss | Alan Noonan (48) |
| 1976 | Bill Stephen | Graham Moss | Graham Moss * | Geoff Blethyn (39) |
| 1977 | Bill Stephen | Ken Fletcher | Simon Madden | Max Crow (38) |
| 1978 | Barry Davis | Ken Fletcher | Ken Fletcher | Wayne Primmer (47) |
| 1979 | Barry Davis | Ken Fletcher | Simon Madden | Terry Daniher (57) |
| 1979 | Barry Davis | Ken Fletcher | Simon Madden | Terry Daniher (57) |
| 1980 | Barry Davis | Simon Madden | Tim Watson | Simon Madden (45) |
| 1981 | Sheedy, KevinKevin Sheedy | Simon Madden | Neale Daniher | Tony Buhagiar (42) |
| 1982 | Sheedy, KevinKevin Sheedy | Neale Daniher | Terry Daniher | Simon Madden (49) |
| 1983 | Sheedy, KevinKevin Sheedy | Terry Daniher | Simon Madden | Terry Daniher (64) |
| 1984 # | Sheedy, KevinKevin Sheedy | Terry Daniher | Simon Madden | Paul Salmon (63) |
| 1985 # | Sheedy, KevinKevin Sheedy | Terry Daniher | Tim Watson | Mark Harvey (48) |
| 1986 | Sheedy, KevinKevin Sheedy | Terry Daniher | Glenn Hawker | Alan Ezard (47) |
| 1987 | Sheedy, KevinKevin Sheedy | Terry Daniher | Mark Thompson | Paul Salmon (43) |
| 1988 | Sheedy, KevinKevin Sheedy | Terry Daniher | Tim Watson | Paul Salmon (37) |
| 1989 | Sheedy, KevinKevin Sheedy | Tim Watson | Tim Watson | Paul Salmon (39) |
| 1990 | Sheedy, KevinKevin Sheedy | Tim Watson | Mark Thompson | Paul Salmon (43) |
| 1991 | Sheedy, KevinKevin Sheedy | Tim Watson | Alan Ezard | Simon Madden (42) |
| 1992 | Sheedy, KevinKevin Sheedy | Mark Thompson | Mark Harvey | Paul Salmon (59) |
| 1993 # | Sheedy, KevinKevin Sheedy | Mark Thompson | Gary O'Donnell [N 1] | Paul Salmon (65) |
| 1994 | Sheedy, KevinKevin Sheedy | Mark Thompson | James Hird | Scott Cummings (32) |
| 1995 | Sheedy, KevinKevin Sheedy | Mark Thompson | James Hird | James Hird (47) |
| 1996 | Sheedy, KevinKevin Sheedy | Gary O'Donnell | James Hird * | James Hird (39) |
| 1997 | Sheedy, KevinKevin Sheedy | Gary O'Donnell | Sean Denham | Matthew Lloyd (63) |
| 1998 | Sheedy, KevinKevin Sheedy | James Hird | Damien Hardwick | Matthew Lloyd (70) |
| 1999 | Sheedy, KevinKevin Sheedy | James Hird / Michael Long | Mark Mercuri | Matthew Lloyd (87) |
| 2000 # | Sheedy, KevinKevin Sheedy | James Hird | Dustin Fletcher | Matthew Lloyd (109) |
| 2001 | Sheedy, KevinKevin Sheedy | James Hird | Jason Johnson | Matthew Lloyd (105) |
| 2002 | Sheedy, KevinKevin Sheedy | James Hird | Mark Johnson | Matthew Lloyd (47) |
| 2003 | Sheedy, KevinKevin Sheedy | James Hird | James Hird / Scott Lucas | Matthew Lloyd (93) |
| 2004 | Sheedy, KevinKevin Sheedy | James Hird | Adam McPhee | Matthew Lloyd (96) |
| 2005 | Sheedy, KevinKevin Sheedy | James Hird | Jason Johnson | Matthew Lloyd (59) |
| 2006 | Sheedy, KevinKevin Sheedy | Matthew Lloyd | Scott Lucas | Scott Lucas (67) |
| 2007 | Sheedy, KevinKevin Sheedy | Matthew Lloyd | James Hird | Matthew Lloyd (62) |
| 2008 | Matthew Knights | Matthew Lloyd | David Hille | Matthew Lloyd (62) |
| 2009 | Matthew Knights | Matthew Lloyd | Jobe Watson | Matthew Lloyd (35) |
| 2010 | Matthew Knights | Jobe Watson | Jobe Watson | Angus Monfries (24) |
| 2011 | James Hird | Jobe Watson | David Zaharakis | Stewart Crameri (34) |
| 2012 | James Hird | Jobe Watson | Jobe Watson | Stewart Crameri (32) |
| 2013 | James Hird | Jobe Watson | Brendon Goddard | Stewart Crameri (30) |
| 2014 | Mark Thompson | Jobe Watson | — | — |
| Source: Essendon Football Club. Last updated: 3 March 2012. |