| 2000 | R1 v Highate | L | 3-2 |
| Whitty | W | 7&6 | |
| Sweetland | W | 7&6 | |
| Brown | L | 4&3 | |
| Porter | L | 4&3 | |
| Riddiford | W | 1up | |
| Ferguson-Jones | W | 1up | |
| Crane | L | 1d | |
| Parry | L | 1d | |
| Rogers | L | 4&3 | |
| Hansford | L | 4&3 | |
| 2001 | R1 v Charterhouse | W | 3.5-1.5 |
| Crane | W | 1up | |
| Sweetland | W | 1up | |
| Riddiford | W | 19th | |
| Ferguson-Jones | W | 19th | |
| Whitty | H | ||
| Coleridge | H | ||
| Staples | L | 2&1 | |
| Hansford | L | 2&1 | |
| Cronk | W | 2&1 | |
| Parry | W | 2&1 | |
| R2 v Ampleforth | W | 3-2 | |
| Crane | W | 4&3 | |
| Sweetland | W | 4&3 | |
| Riddiford | W | 4&3 | |
| Ferguson-Jones | W | 4&3 | |
| Whitty | H | ||
| Coleridge | H | ||
| Staples | H | ||
| Hansford | H | ||
| Cronk | W | 5&4 | |
| Parry | W | 5&4 | |
| R3 v Merchiston | L | 3.5-1.5 | |
| Staples | L | 3&2 | |
| Hansford | L | 3&2 | |
| Crane | L | 5&4 | |
| Sweetland | L | 5&4 | |
| Riddiford | W | 2up | |
| Ferguson-Jones | W | 2up | |
| Whitty | H | ||
| Coleridge | H | ||
| Cronk | L | 2d | |
| Parry | L | 2d | |
| 2002 | R1 v Haileybury | W | 3-2 |
| Crane | W | 1up | |
| Sweetland | W | 1up | |
| Whitty | L | 6&5 | |
| Coleridge | L | 6&5 | |
| Riddiford | L | 1d | |
| Ferguson-Jones | L | 1d | |
| Rogers | W | 6&5 | |
| Hansford | W | 6&5 | |
| Cronk | W | 5&4 | |
| Parry | W | 5&4 | |
| R2 v Rugby | L | 2-3 | |
| Crane | L | 2&1 | |
| Sweetland | L | 2&1 | |
| Whitty | W | 4&3 | |
| Hansford | W | 4&3 | |
| Rogers | L | 3&2 | |
| Williams R | L | 3&2 | |
| Riddiford | W | 3&2 | |
| Ferguson-Jones | W | 3&2 | |
| Cronk | L | 4&3 | |
| Parry | L | 4&3 | |
| 2003 | R1 v Malvern | ||
| Porter | W | 1up | |
| Rosenberg | W | 1up | |
| Riddiford | L | 1d | |
| Ferguson-Jones | L | 1d | |
| Whitty | H | ||
| Parry | H | ||
| Crane | L | 5&4 | |
| Sweetland | L | 5&4 | |
| Rogers | L | 7&6 | |
| Hansford | L | 7&6 | |
| 2004 | R1 v Clifton | L | 2-3 |
| Crane | W | 4&3 | |
| Sweetland | W | 4&3 | |
| Whitty | L | 5&4 | |
| Coleridge | L | 5&4 | |
| Ferguson-Jones | L | 4&3 | |
| Parkes | L | 4&3 | |
| Rosenberg | L | 20th | |
| Parry | L | 20th | |
| Riddiford | W | 2&1 | |
| Hansford | W | 2&1 | |
| 2005 | R1 v The Leys | W | 3.5-1.5 |
| Crane | W | 3&2 | |
| Sweetland | W | 3&2 | |
| Davies JC | W | 8&7 | |
| Ferguson-Jones | W | 8&7 | |
| Whitty | H | ||
| Riddiford | H | ||
| Rosenberg | W | 3&2 | |
| Parry | W | 3&2 | |
| Porter | L | 3&2 | |
| Hansford | L | 3&2 | |
| R2 v Tonbridge | L | 0.5-4.5 | |
| Crane | L | 4&3 | |
| Sweetland | L | 4&3 | |
| Whitty | L | 1d | |
| Riddiford | L | 1d | |
| Davies JC | H | ||
| Ferguson-Jones | H | ||
| Rosenberg | L | 4&3 | |
| Parry | L | 4&3 | |
| Parkes | L | 8&7 | |
| Rogers | L | 8&7 | |
| 2006 | R1 v Rossall | L | 0.5-4.5 |
| Crane | L | 3&2 | |
| Porter | L | 3&2 | |
| Davies JC | H | ||
| Ferguson-Jones | H | ||
| Whitty | L | 3&2 | |
| Sweetland | L | 3&2 | |
| Rosenberg | L | 4&3 | |
| Parry | L | 4&3 | |
| Connelly | L | 4&3 | |
| Riddiford | L | 4&3 | |
| 2007 | R1 v Eastbourne | W | 3.5-1.5 |
| Davies JC | W | 3&2 | |
| Ferguson-Jones | W | 3&2 | |
| Crane | W | 2&1 | |
| Porter | W | 2&1 | |
| Connelly | H | ||
| Riddiford | H | ||
| Whitty | L | 4&3 | |
| Schofield | L | 4&3 | |
| Rosenberg | W | 3&2 | |
| Parry | W | 3&2 | |
| R2 v Tonbridge | L | 1-4 | |
| Crane | L | 3&2 | |
| Porter | L | 3&2 | |
| Davies JC | H | ||
| Ferguson-Jones | H | ||
| Connelly | L | 3&2 | |
| Riddiford | L | 3&2 | |
| Whitty | H | ||
| Schofield | H | ||
| Rosenberg | L | 6&5 | |
| Parry | L | 6&5 | |
| 2008 | R1 v Merchiston | L | 0.5-4.5 |
| Hansford | L | 5&3 | |
| Janmohamed | L | 5&3 | |
| Crane | L | 5&3 | |
| Whitty | L | 5&3 | |
| Porter | L | 3&2 | |
| Ferguson-Jones | L | 3&2 | |
| Connelly | L | 5&4 | |
| Riddiford | L | 5&4 | |
| Parry | H | ||
| Rosenberg | H | ||
| 2009 | R1 v Eton | L | 1.5-3.5 |
| Parry | L | 6&5 | |
| Rosenberg | L | 6&5 | |
| Davies JC | W | 1up | |
| Whitty | W | 1up | |
| Williams R | L | 4&3 | |
| Riddiford | L | 4&3 | |
| Crane | H | ||
| Janmohamed | H | ||
| Kendrick | L | 5&4 | |
| Connelly | L | 5&4 |
OLD CRANLEIGHAN GOLFING SOCIETY