The club, composed of Caulfield Grammar School alumni is, the (equal) second oldest consecutively competing team in the Victorian Amateur Football Association (VAFA).

On Monday, 22 March 1920, a meeting of the (then) Metropolitan Amateur Football Association decided to resume the inter-club competition that it had suspended for the duration of World War I at the end of the 1915 season.

On Saturday, 12 September 1925, coached by former VFL senior umpire, Brighton coach, and Brunswick, Prahran, Brighton, and St Kilda footballer, Fred Turnbull and led by Ian Howell, Caulfield Grammarians beat Teachers' College by 37 points, 13.14 (92) to 8.7 (55) to win the B Section premiership at the Old Scotch Oval; the team's full forward, Eric Dakin, kicked four goals in the Grand Final to bring his season's total to 125 goals.

Under the rules prevailing at the time (see amended Argus system), because Old Caulfield Grammarians were the "minor premiers" at the end of the home-and-away season (they had only lost two matches in the entire season), the team's defeat of Teachers' College in this match meant that there was no need for a "Grand Final" to decide the premiership.

[14] On Saturday, 3 September 1949, coached by Wally Crabtree and led by Sam “Mocca" Johnstone, Caulfield Grammarians beat Murrumbeena Football Club by 29 points, 9.10 (64) to 5.5 (35) to win the D Section Grand Final.

[15] On Saturday, 5 September 1953, coached by Ian Hibbins and led by Ron Ashbolt, Caulfield Grammarians beat Powerhouse Football Club by two points, 10.9 (69) to 9.13 (67) to win the C Section Grand Final.

[16] On Saturday, 9 September 1961, coached by John Wilson and led by Bill O'Halloran, Caulfield Grammarians beat West Brunswick Football Club by 15 points, 10.7 (67) to 8.4 (52) to win the D Section Grand Final at Ross Gregory Reserve.

[18] Coburg had been the strong favourite going into the match, and the victory was the result of an exceptional team effort, made all the more worthwhile in the context of the Fields' inaccurate kicking.

Caulfield trailed by 5 points at the main break after a very tight first half, in which Captain Dean Anderson had to leave the field with a nasty head wound.

Jason Cowlishaw then kicked 2 quick goals to get the Fields back into it and when Glen Harrison dribbled one through with only seconds left, the game was tied.

On Saturday, 17 September 2011, coached by Steve Lawrence and led by Simon Widjaja, Caulfield Grammarians defeated St Bernards Old Collegians at Elsternwick Park by 33 points, 17.12 (114) to 12.9 (81) to win the 2011 B Section Premiership.

On Sunday, 18 August 2019, coached by Mitch Dupljanin and led by Toni Hamilton, Caulfield Grammarians defeated Old Xaverians at Mentone Playing Fields by 14 points, 2.2 (14) to 0.0 (0) to win the 2019 Women's B Section Premiership.

On Saturday, 21 September 2019, coached by Simon Williams and led by Tim Nixon, Caulfield Grammarians defeated Old Scotch Football Club at Elsternwick Park by 92 points, 17.22 (124) to 4.8 (33) to win the 2019 B Section Premiership.

Caulfield Grammarians, coached by Ray Keane and led by Nigel Caple, beat Albanvale by 24 points, 20.12 (132) to 17.6 (108) to win the 1990 U/19 Section 3 Grand Final.

Caulfield Grammarians, coached by Chris Mathieson and led by Richard Foote, beat Werribee by 68 points at Warrawee Park, 17.13 (115) to 6.11 (47) to win the 2001 U/19 Section 2 Grand Final.

Caulfield Grammarians, coached by Will Bowes and led by Aiden Clarke, beat Ormond Amateur Football Club by 28 points at Trevor Barker Oval, 9.13 (69) to 5.11 (41) to win the 2010 C Section Grand Final.

Caulfield Grammarians, coached by Shaun Frazier and led by Simon Cunliffe, beat Mazenod Old Collegians by 26 points at Elsternwick Park, 8.16 (64) to 5.8 (38) to win the 2010 Club XVII South Section Grand Final.

Caulfield Grammarians, coached by Josh McCahon and led by James Small, beat Parkdale by 24 points at Trevor Barker Oval, 13.14 (92) to 8.20 (68) to win the 2015 U/19 Section 2 Grand Final.

Caulfield Grammarians, coached by Josh McCahon and led by Myles Spielvogel, beat Parkdale by 14 points at Trevor Barker Oval, 12.6 (78) to 9.10 (64) to win the 2016 U/19 Section 2 Grand Final.

Caulfield Grammarians, coached by Will Bowes and led by Nick O'Connor, beat Marcellin Old Collegians by 39 points at Elsternwick Park, 14.6 (90) to 7.9 (51) to win the 2016 C Thirds Section Grand Final.

Caulfield Grammarians, coached by Seb Gotch and led by Damien Hay and Rob Handel, beat Marcellin Old Collegians by 38 points at Casey Fields, 9.17 (71) to 5.3 (33) to win the 2017 C Reserves Section Grand Final.

Caulfield Grammarians, coached by Will Bowes and led by Aiden Clarke, beat De La Salle Old Collegians by 39 points at Box Hill City Oval, 9.7 (61) to 3.4 (22) to win the 2019 B Thirds Section Grand Final.

Caulfield Grammarians, coached by Lachlan Rayner, Daniel Sherman, and Stephen Kendall, led by Harry Neave, progressed to a 10–1 finish in a COVID interrupted campaign.

Caulfield Grammarians, coached by Marc Cassidy and led by Jack Pinder, beat St Mary’s Salesian by 21 points at Trevor Barker Oval, 11.12 (78) to 7.15 (57) to win the 2024 U19 Division 4 Grand Final.