The Caulfield Grammarians Football Club is an Australian rules football club based in Caulfield East, Victoria. The club, composed of Caulfield Grammar School alumni is, the (equal) second oldest consecutively competing team in the Victorian Amateur Football Association (VAFA).

The team entered the competition in 1920, and has competed continuously since that time (competition was suspended from 1940 to 1945 during World War II). In 2020, the club’s centenary year, all 6 teams were in their respective A Grades.

Their home ground is the Glen Huntly Oval, at the corner of Neerim Road and Booran Road.

Caulfield Grammar "Old Boys" From time to time various teams of "Old Boys" were selected to play against the school's team. The first of these matches took place on 15 August 1889, and matches such as these took place on a regular basis from 1907 to 1914 (when the matches ceased due to World War I).

Caulfield Grammarians Football Club The Caulfield Grammarians Football Club was founded in early 1920. Caulfield Grammar School's headmaster, Walter Murray Buntine, was elected as its inaugural president. Buntine gave the team access to all of the schools sporting facilities for its training, and he allowed the team to use the school's oval as its home ground.

Metropolitan Amateur Football Association 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.In late 1915, the Metropolitan Amateur Football Association announced that it had suspended its competition, and would not resume the competition until the war had ended: Old Boy, "District Football: The League's Preparations", The Argus, (Wednesday, 8 December 1915), p.13. The MAFA announced that the re-formed competition would be between four of the "pre-war" clubs, Collegians Football Club, South Yarra Amateur Football Club, Elsternwick Football Club, and Melbourne University Football Club (later University Blacks), and four "new clubs": Old Melburnians, Old Caulfield Grammarians, Melbourne Swimming Club Football Club and the Teachers’ College Football Club.Football: Metropolitan Amateur Association, The Argus, (Friday, 26 March 1920), p.11.

In their first competition match, on Saturday 15 May 1920, Old Caulfield Grammarians were narrowly beaten 7.11 (53) to 6.16 (50) by Collegians.Metropolitan Amateur Association, The Argus, Monday 17 May 1920), p.5.

Their second competition match was against Teachers’ College on Saturday, 22 May 1920, at the Caulfield Grammar School Oval. Old Caulfield Grammarians won convincingly, 12.17 (89) to 3.7 (25).Football: Metropolitan Junior Association, The Age, (Monday, 24 May 1920), p.10.

A 1921 press report of the team's Metropolitan Amateur Football Association match against Hampton refers to the team as Old Caulfield Collegians;Metropolitan Association, The Argus, (Monday 30 May 1921), p.3. it is unclear whether this was an inadvertent typographical error — such as the South Australian newspaper references to Hans Ebeling (C.G.S. 1919–1922), as "the old Caulfield Collegian"For example, Colts in Melbourne: Victoria's Substantial Lead, The (Adelaide) Register, Friday, 8 February 1924), p.11. — or a case of the reporter confusing the Old Caulfield Grammarians Football Club with an earlier team known as "Caulfield Collegians" that seems to have, from time to time, contained a large percentage of Caulfield Grammar "Old Boys".There are various reports relating to the "Caulfield Collegians" over an extended period; e.g., 1894, playing from Elsternwick (Football: Today's Matches, The Caulfield and Elsternwick Leader, (Saturday, 5 May 1894), p.5); 1895, playing against Brighton Park (Football: Park vs. Collegians, Oakleigh Leader, (Saturday, 18 May 1895, p.2); 1896, playing against Diamond Creek (Football, Evelyn Observer, and South and East Bourke Record, (Friday, 29 May 1896), p.5); 1903, playing against Frankston (Sporting Notes: Football, Mornington Standard, (Saturday, 11 July 1903), p.4).

In 1904, the Victorian press reported that Caulfield Collegians Football Club, centred on Caulfield Grammar School, that played its matches on the school grounds, was competing in a competition conducted by The Colleges' Football Association:Colleges' Association, The Age (Wednesday, 28 September 1904), p.11. Great things are expected of … this association … formed at the beginning of the season … [and] composed of teams from various well-known schools, and one from the University … as it fills a long-felt want in providing games on Saturdays for those who, although they have left school, do not wish to surrender its healthy amusements.Old Boy, The Australasian, (Saturday, 25 June 1904), p.20.

In the competition's first season (1904), Caulfield Collegians Football Club was the premier team;Old Boy, "College Sports: Weekly Jottings", The Australasian, (Saturday, 12 November 1904), p.23. and, in the second season (1905), Sherwood Collegians were premiers.Football, The Age, (Tuesday, 19 September 1905), p.8. There is no trace of any further competition conducted by the Colleges' Football Association.

VAFA Senior Premierships

1925 – B Grade 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.Metropolitan Amateurs: Old Caulfield win B Section, The Argus, (Monday 14 September 1925), p.17.

Goals: E.Dakin 4, Cassidy 4, Dunstan 2, Kohn 2, Chaffey. Best: Pie, Matheson, Cassidy, Jones, Dunstan, Donaldson.

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.Metropolitan Amateurs: Old Caulfield B Section Premiers, The Age, (Monday 14 September 1925), p.15. (Note with this link (the newspaper has been scanned sideways) you must move to "page 23" and then scroll down until you reach column F of page 15 of the 14 September 1925 issue.)

1949 – D Grade 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. Better players on the day included ruckman Bruce Small, centreman Ian Felsenthal, full forward Todd Cassidy and former St Kilda player Irving Davidson.Blacks Outlast Old Scotch, The Argus, (Monday, 5 September 1949), p.14.

1953 – C Grade 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.Weekend Sport Details: Amateur Football, The Argus, (Monday, 7 September 1953), p.13.

1961 – D Grade 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. Caulfield had lost the 2nd Semi Final to West Brunswick in a tight game 2 weeks earlier, before beating Fairfield in the Preliminary Final to earn a rematch. Caulfield started the game well with Tony Johnstone kicking the first 2 goals of the game. Nigel Kendall kicked 5 goals and full back John Caspers was named best on ground.Collegians Too Good for Blacks,The Age, (Monday, 11 September 1961), p.18.

Goals: N.Kendall 5, A.Johnstone 2, W.O'Halloran 2, R.Dixon. Best: J.Caspers, N.Kendall, M.Northeast, W.O'Halloran, A.Johnstone, T.Tootell.

1970 – A Grade After having lost the 1967 and 1968 A Grade Grand Finals to Old Paradians by 18 points and 75 points respectively, on Saturday, 12 September 1970, coached by John Wilson (it was his 200th match as coach) and led by Tony Pyman (Club Captain David Williams missed the game with injury), Caulfield Grammarians held off a strongly finishing Coburg Amateurs team to win the 1970 A Section Premiership by two points, 14.18 (102) to 15.10 (100).Caulfield by Two Points, The Age, (Monday, 14 September 1970), p.17. 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. Goals: G.Atchinson 2, J.Butcher 2, A.Lester 2, P.Hore 2, P.McLaughlin, L.McNicol, J.Lane, J.Hore, R.Allen, B.Morphett. Best: A.Lester, J.Lane, K.Barker, L.McNicol, G.Tootell, B.Morphett.

1983 – C Grade On Saturday, 3 September 1983, coached by A.C.Poore and led by G. Stone, Caulfield Grammarians beat Parkside Football Club by 66 points, 20.16 (136) to 8.22 (70) to win the C Section Grand Final, with full-forward Dave Matthews kicking 10 goals in the Grand Final, for a total of 114 in the entire premiership season (viz., including the finals).Blues Coast to Amateur Final, The Age, (Monday, 5 September 1983), p.25. Goals: D.Matthews 10, C.Cooney 4, G.Voyage 2, R.Sisson 2, R.Berzins, J.Kanis. Best: M.Sisson, J.Kanis, D.Matthews, C.Cooney, R.Fish, C.Stone.

1998 – E Grade Caulfield Grammarians, coached by Geoff Reilly and led by Dean Anderson, beat Old Camberwell Grammarians by 32 points at Central Reserve, 11.14 (80) to 7.6 (48) to win the 2000 E Blue Section Grand Final. 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. He returned in the second half to inspire his team as Caulfield slowly put the game out of Camberwell's reach. Goals: B.Hall 5, D.Anderson, B.Baxter, W.Bowes, M.DiCrosta, D.Lowe, H.Vella. Best: D.Synman, W.Bowes, N.Lubransky, N.Brohier, T.Royals, D.Anderson.

2000 – D Grade Caulfield Grammarians, coached by Dean Anderson and led by Nigel Brohier, beat Old Essendon Grammarians at Box Hill City Oval by 125 points, 26.13 (169) to 6.8 (44) to win the 2000 D Section Grand Final. Stephen Amiet was awarded the J.W.Manton Medal for being voted best on ground. Goals: S.Amiet 9, A.Will 6, D.Rosman 4, J.Margerison 2, J.Cowlishaw 2, G.Harrison, D.Pearce, T.Royals. Best: S.Amiet, D.Pearce, J.Whitmee, S.Widjaja, D.Synman, M.Liddell.

This one sided contest was a far cry from the thrilling 2nd Semi Final between these two sides that was played a fortnight earlier. After a tight first half, Old Essendon had taken control of the game and led by 4 goals with minutes to play. 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. Inspired by this late comeback, Caulfield dominated extra time to run out 19 point winners.

This year also saw Caulfield win the club's first Reserves Premiership, with a 51 point win over Old Essendon, 13.12 (90) to 5.9 (39). The highlight of the game being the sealing goal by club legend Scott Williams, on the run from 49m out. Coached by Kornal Dachs and led by Joe Santiago, this was redemption for much of the side who had narrowly lost in the 1998 decider.

2011 – B Grade