| 1st Round | |||||
| 28.Oct.2023 | Lancing Old Boys | 1 - 4 | Old Brentwoods | ||
| 04.Nov.2023 | KCS Old Boys | 2 - 1 | Old Rugbeians | ||
| 28.Oct.2023 | Old Kimboltonians | W - L | Old Kingstonians | ||
| 28.Oct.2023 | Old Malvernians | 0 - 6 | Old Foresters | ||
| 28.Oct.2023 | Old Shirburnians | 1 - 3 | Old Bradfieldians | ||
| 28.Oct.2023 | Old Etonians | 8 - 0 | Old Haberdashers | ||
| 28.Oct.2023 | Old Berkhamstedians | 2 - 5 | Old Alleynians | ||
| 28.Oct.2023 | Old Harrovians | 2 - 3 | Old Chigwellians | ||
| 28.Oct.2023 | Old Wykehamists | 3 - 1 | Old Radleians | ||
| 28.Oct.2023 | Old Ardinians | 4 - 2 | Old Salopians | ||
| 28.Oct.2023 | Old Westminsters | 2 - 2 | Old Tonbridgians | ||
| 11.Nov.2023 | Old Tonbridgians | 3 - 2 | Old Westminsters | ||
| 28.Oct.2023 | Old Merchant Taylors | 3 - 0 | Old Amplefordians | ||
| 28.Oct.2023 | Old Johnians | 3 - 1 | Old Sennockians | ||
| 28.Oct.2023 | Old Cholmeleians | L - W | Old Aldenhamians | ||
| 2nd Round | |||||
| 16.Dec.2023 | Old Reptonians | 3 - 1 | Old Brentwoods | ||
| 16.Dec.2023 | KCS Old Boys | 8 - 2 | Old Kimboltonians | ||
| 16.Dec.2023 | Old Foresters | 4 - 5 | Old Bradfieldians | ||
| 16.Dec.2023 | Old Etonians | 0 - 1 | Old Alleynians | ||
| 16.Dec.2023 | Old Chigwellians | 4 - 2 | Old Wykehamists | ||
| 16.Dec.2023 | Old Ardinians | 2 - 3 | Old Tonbridgians | ||
| 27.Jan.2024 | Old Merchant Taylors | 1 - 2 | Old Carthusians | ||
| 16.Dec.2023 | Old Johnians | 1 - 0 | Old Aldenhamians | ||
| Quarter-Finals | |||||
| 17.Feb.2024 | Old Reptonians | 4 - 0 | KCS Old Boys | ||
| 10.Feb.2024 | Old Bradfieldians | 2 - 3 | Old Alleynians | ||
| 10.Feb.2024 | Old Chigwellians | 2 - 4 | Old Tonbridgians | ||
| 17.Feb.2024 | Old Carthusians | 4 - 0 | Old Johnians | ||
| Semi-Final | |||||
| 23.Mar.2024 | Old Reptonians | 3 - 2 | Old Alleynians | ||
| 06.Apr.2024 | Old Tonbridgians | 3 - 2 | Old Carthusians | ||
| Final (Merchant Taylors School, Northwood) | |||||
| 20.Apr.2024 | Old Reptonians | 1 - 0 | Old Tonbridgians | ||