| 2020 | NOT PLAYED | ||
| 2021 | R1 v Marlborough | L | 2-3 |
| Boyle | W | 3&2 | |
| Pickford | W | 3&2 | |
| Richards | W | 2&1 | |
| Montgomerie | W | 2&1 | |
| Kendrick | L | 2&1 | |
| Ferguson-Jones | L | 2&1 | |
| Cary | L | 2&1 | |
| C Moore | L | 2&1 | |
| Whitty | L | 19th | |
| Hansford | L | 19th | |
| 2022 | R1 v Merchiston | W | 3.5-1.5 |
| Boyle | L | 5&4 | |
| Pickford | L | 5&4 | |
| Whitty | W | 3&1 | |
| Millburn Fryer | W | 3&1 | |
| C Moore | W | 2&1 | |
| Kendrick | W | 2&1 | |
| Cary | W | 2&1 | |
| Ferguson-Jones | W | 2&1 | |
| Richards | H | ||
| Montgomerie | H | ||
| R2 v Framlingham | W | 4-1 | |
| Boyle | W | 1up | |
| Pickford | W | 1up | |
| Whitty | W | 7&6 | |
| Millburn Fryer | W | ||
| C Moore | W | 6&5 | |
| Kendrick | W | 6&5 | |
| Cary | H | ||
| Ferguson-Jones | H | ||
| Richards | W | 3&2 | |
| Montgomerie | W | 3&2 | |
| R3 v Radley | L | 0.5-4.5 | |
| Boyle | L | 5&4 | |
| Pickford | L | 5&4 | |
| Whitty | L | 2&1 | |
| Millburn Fryer | L | 2&1 | |
| Cary | L | 4&3 | |
| Ferguson-Jones | L | 4&3 | |
| Richards | H | ||
| Montgomerie | H | ||
| C Moore | L | 5&3 | |
| Kendrick | L | 5&3 | |
| 2023 | R1 v Fettes | W | 3.5-1.5 |
| Boyle | W | 5&3 | |
| Pickford | W | 5&3 | |
| Richards | W | 4&3 | |
| Millburn-Fryer | W | 4&3 | |
| C Moore | H | ||
| Kendrick | H | ||
| F Moore | W | 4&3 | |
| Ferguson-Jones | W | 4&3 | |
| Whitty | L | 5&4 | |
| JSF Wilkinson | L | 5&4 | |
| R2 v Bradfield | W | 3-2 | |
| Boyle | L | 3&1 | |
| Pickford | L | 3&1 | |
| Whitty | W | 2&1 | |
| JSF Wilkinson | W | 2&1 | |
| F Moore | W | 4&3 | |
| Ferguson-Jones | W | 4&3 | |
| Richards | L | 3&2 | |
| Millburn-Fryer | L | 3&2 | |
| C Moore | W | 19th | |
| Kendrick | W | 19th | |
| R3 v Canford | L | 4-1 | |
| Boyle | L | 5&4 | |
| Pickford | L | 5&4 | |
| Whitty | L | 3&2 | |
| JSF Wilkinson | L | 3&2 | |
| F Moore | L | 3&2 | |
| Ferguson Jones | L | 3&2 | |
| Richards | H | ||
| Millburn-Fryer | H | ||
| C Moore | H | ||
| Kendrick | H | ||
| 2024 | R1 v St Bees | W | 4-1 |
| Pickford | W | 19th | |
| Boyle | W | 19th | |
| Richards | L | 2&1 | |
| Montgomerie | L | 2&1 | |
| Ferguson Jones | W | 2&1 | |
| F C Moore | W | 2&1 | |
| G E M Wilkinson | W | 8&7 | |
| Millburn-Fryer | W | 8&7 | |
| C D Moore | W | 3&2 | |
| Kendrick | W | 3&2 | |
| R2 v Stonyhurst | W | 3.5-1.5 | |
| G E M Wilkinson | W | 1up | |
| Millburn-Fryer | W | 1up | |
| Ferguson Jones | W | 6&5 | |
| Whitty | W | 6&5 | |
| C D Moore | W | 3&2 | |
| Kendrick | W | 3&2 | |
| Pickford | L | 3&1 | |
| Boyle | L | 3&1 | |
| Richards | H | H | |
| Montgomerie | H | H | |
| R3 v Greshams | W | 4-1 | |
| Pickford | W | 2&1 | |
| F C Moore | W | 2&1 | |
| Richards | W | 1up | |
| Montgomerie | W | 1up | |
| G E M Wilkinson | W | 4&3 | |
| Millburn Fryer | W | 4&3 | |
| Ferguson Jones | W | 3&2 | |
| Whitty | W | 3&2 | |
| C D Moore | L | 4&3 | |
| Kendrick | L | 4&3 | |
| QF v Brighton | W | 3-2 | |
| Pickford | W | 2up | |
| F C Moore | W | 2up | |
| Richards | L | 5&4 | |
| Montgomerie | L | 5&4 | |
| G E M Wilkinson | L | 5&3 | |
| Millburn Fryer | L | 5&3 | |
| Ferguson Jones | W | 3&2 | |
| Whitty | W | 3&2 | |
| C D Moore | W | 4&3 | |
| Kendrick | W | 4&3 | |
| SF v Bedford | L | 3-2 | |
| Pickford | W | 1up | |
| F C Moore | W | 1up | |
| G E M Wilkinson | L | 3&2 | |
| Millburn Fryer | L | 3&2 | |
| Richards | L | 19th | |
| Montgomerie | L | 19th | |
| Ferguson Jones | W | 4&3 | |
| Whitty | W | 4&3 | |
| C D Mooore | L | 3&2 | |
| Kendrick | L | 3&2 | |
OLD CRANLEIGHAN GOLFING SOCIETY