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 lead 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.[13]
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.[14]
1949 – D Grade
On Saturday, 3 September 1949, coached by Wally Crabtree and lead 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.[15]
1953 – C Grade
On Saturday, 5 September 1953, coached by Ian Hibbins and lead 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]
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.[17]
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 lead by Tony Pyman (Club Captain David Williams missed the game with injury), Caulfield Grammarians held off a strongly finishing Coburg Amateurs Football Club team to win the 1970 A Section Premiership by two points, 14.18 (102) to 15.10 (100).[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.
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 lead 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).[19]
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 lead 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 lead 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 lead 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 lead by Joe Santiago, this was redemption for much of the side who had narrowly lost in the 1998 decider.
2011 – B Grade
On Saturday, 17 September 2011, coached by Steve Lawrence and lead 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.[20][21] Mark Liddell was awarded the Ian Cordner medal for being voted best on ground.
Goals: J.Perkins 5, G.Winter 3, C.Johnston 3, T.O'Sullivan 2, S.Garrubba 2, J.Shanahan, G.Meredith.
Best: M.Liddell, J.Shanahan, S.Garrubba, S.Wood, R.Lewis, J.Perkins.
2019 – Women's B Grade
On Sunday, 18 August 2019, coached by Mitch Dupljanin and lead 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. Irena Malliaras was awarded the medal for being voted best on ground. The game was played in incredibly poor weather, which made scoring very difficult. This was Caulfield Grammarians' first women's premiership and achieved in only their 3rd year of existence. It also returns the club to A Grade, only 1 year after being relegated.
Goals: M.White, K.Macqueen.
Best: J.Harley, E.Baxter, I.Malliaras, T.Hamilton, B.Fox, M.Anthony.
2019 – B Grade
On Saturday, 21 September 2019, coached by Simon Williams and lead 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. Lachlan Stephens was awarded the Ian Cordner medal for being voted best on ground.
Goals: W.Osborn 3, L.Stephens 2, B.Goddard 2, J.Dobosz 2, N.Page 2, J.Wallace 2, W.Barker, T.Green, T.Nixon, T.Thompson.
Best: J.Webster, L.Stephens, D.Reilly, J.Wallace, W.Edwards, W.Osborn.
VAFA Other Premierships
1990 – U/19 Section 3
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. Clint Baxter was voted best afield.
Goals: N.Caple 6, C.Baxter 6, C.Garraway 4, W.Bryne 2, G.Harrison, A.Kouvaris.
Best: C.Baxter, N.Caple, C.Simpson, R.Royals, J.Dight, N.Cox..
2000 – D Grade Reserves
Caulfield Grammarians, coached by Kornal Dachs and led by Joe Santiago, beat Old Essendon Grammarians by 51 points at Box Hill City Oval, 13.12 (90) to 5.9 (39) to win the 2000 D Reserves Section Grand Final.
Goals: N/A.
Best: N/A.
2001 – U/19 Section 2
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 lead all day, after a much closer 2nd Semi Final 2 weeks earlier.
Goals: A.Bruhn 3, R.Foote 3, L.Schneider 3, A.Sinclair 2, P.Roberts, L.Browne, T.Foster, C.Hooper, K.Boehm, N.Fallu.
Best: L.Schneider, M.Pennycuick, K.Boehm, W.Frost, I.Glass, T.Foster.
2002 – C Grade Reserves
Caulfield Grammarians, coached by Martin DiCrosta and led by John Jacobs, beat Old Camberwell Grammarians by 26 points at Elsternwick Park, 9.11 (65) to 5.9 (39) to win the 2002 C Reserves Section Grand Final. Caulfield led all day after a strong first quarter into the breeze. Mark Pennycuick was voted best on ground.
Goals: M.Pennycuick 4, J.Dalwood 2, S.Kendall, J.Margerison, J.Cowlishaw.
Best: M.Pennycuick, S.Thompson, S.Sant, G.Erickson, J.Jacobs, J.Dalwood.
2010 – C Grade Reserves
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. In what was a tight affair, Caulfield took the lead in the 2nd quarter and never relinquished it for the rest of the game. Ruckman Nick Dorman was named best on ground by the umpires.
Goals: D.Spanos 2, J.Kremmer 2, A.Strain 2, R.Foote, D.Allanson, J.McCahon.
Best: R.Foote, A.Strain, N.Dorman, A.Lawson, A.Townsend, J.Kremmer.
2010 – Club XVIII South
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. The umpires selected Simon Cunliffe as best on ground.
Goals: G.Vanderkruk 4, B.Scott 2, A.Bednarek, N.Guyatt.
Best: N.Guyatt, G.Crathern, J.Pitts, S.Cunliffe, A.Bednarek, P.Farmer.
2015 – U/19 Section 2
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 had finished the season in 4th and only won the 1st Semi Final by 1 point against Fitzroy on their run to the Grand Final.
Goals: L.Topp 3, F.McEvoy 3, T.Tonkin 2, T.Stephenson, J.Small, N.Answerth, K.Malignaggi, J.Toniolo.
Best: J.Toniolo, F.McEvoy, T.Smith, C.Bold, Z.Amos, J.Stewart.
2016 – U/19 Section 2
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. This was the first time in club history that a team had gone back to back.
Goals: M.Spielvogel 3, M.Ball 2, S.Dorevitch, L.Edwards, B.Fynmore, N.Baltas, J.Toniolo, B.Kuang, O.Gagiero.
Best: O.Allis, L.Harris, Z.Amos, M.Simpson, M.Spielvogel, J.Lewis.
2016 – C Grade Thirds
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. This was a particularly sweet win as the previous season the club didn't have the personnel to even field a Thirds team.
Goals: A.Strain 5, S.Richards 2, C.Hogan 2, J.Smart, M.Wood, N.O'Connor, W.Kingwill, B.Chilko.
Best: J.Anderson, C.Hogan, M.Linklater, A.Strain, J.Smart, K.Malignaggi.
2017 – C Grade Reserves
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.
Goals: W.Kingwill 4, R.Handel 2, J.Small, H.Marshall, D.Hay.
Best: T.Smith, R.Harris, J.Anderson, W.Kingwill, L.Everett, D.Hay.
2019 – B Grade Thirds
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. Veteran back Andrew Spittal was named best on ground by the umpires.
Goals: M.Ball 4, R.Handel 2, Z.Parsons, J.Waldron, J.Small.
Best: H.Mills, M.Ball, W.Ingham, S.Pincus, E.McDonald, J.Easton.
2021 – U/19 Section 1
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. They were awarded the 2021 U19 Premier Minor Premiership, the first piece of silverware ever recorded for the club in U19 Section 1.
