| First Round | ||||||
| 11 | 14.Nov | Old Worthians |  | 12:00 |  | Old Johnians II |
| 12 | 07.Nov | Old Kingstonians |  | 13:30 |  | Old Cranleighans |
| 13 | 07.Nov | Old Brentwoods III |  | 10:30 |  | Old Shirburnians |
| 14 | 14.Nov | Old Alleynians III |  | TBC |  | Old Oundelians |
| 15 | 07.Nov | Old Felstedians |  | TBC |  | Old Chigwellians II |
| 16 | 07.Nov | Old Bradfieldians II |  | TBC |  | Old Stoics |
| Second Round | ||||||
| 21 | 05.Dec | Winner 16 |  |  | KCS Old Boys II | |
| 22 | 28.Nov | Old Tonbridgians II |  | 11:00 |  | Old Epsomians |
| 23 | 05.Dec | Old Haberdashers |  | | Winner 14 | |
| 24 | 05.Dec | Winner 12 | |  | Old Brentwoods II | |
| 25 | 05.Dec | Old Canfordians |  | TBC |  | Old Westminsters II |
| 26 | 05.Dec | Old Cholmeleians II |  | | Winner 13 | |
| 27 | 05.Dec | Old Berkhamstedians II |  | | Winner 15 | |
| 28 | 05.Dec | Old Harrovians II |  | | Winner 11 | |
| Third Round | ||||||
| 31 | 23.Jan | Winner 28 | | | Winner 27 | |
| 32 | 23.Jan | Old Westminsters | | | Winner 24 | |
| 33 | 23.Jan | Winner 25 | | | Old Berkhamstedians | |
| 34 | 23.Jan | Old Albanians |  | 10:00 |  | Lancing Old Boys |
| 35 | 23.Jan | Old Alleynians II | | | Winner 21 | |
| 36 | 23.Jan | Old Etonians II |  | | Winner 22 | |
| 37 | 23.Jan | Old Sennockians |  | | Winner 26 | |
| 38 | 23.Jan | Old Carthusians II |  | | Winner 23 | |
|