1st XV
| 16 September 2023 | Old Tiffinians | V | Old Cranleighans | L | HWO |
| 23 September 2023 | Old Cranleighans | V | Weybridge Vandals | L | 5 – 78 |
| 30 September 2023 | Kingston | V | Old Cranleighans | L | 34 – 7 |
| 7 October 2023 | Old Cranleighans | V | Hove | L | 17 – 24 |
| 14 October 2023 | Old Walcountians | V | Old Cranleighans | ||
| 21 October 2023 | Old Cranleighans | V | Twickenham | ||
| 4 November 2023 | East Grinstead | V | Old Cranleighans | ||
| 11 November 2023 | Old Cranleighans | V | Trinity | ||
| 18 November 2023 | Teddington | V | Old Cranleighans | ||
| 2 December 2023 | Old Cranleighans | V | KCS Old Boys | ||
| 9 December 2023 | Eastbourne | V | Old Cranleighans | ||
| 16 December 2023 | Weybridge Vandals | V | Old Cranleighans | ||
| 6 January 2024 | Old Cranleighans | V | Kingston | ||
| 13 January 2024 | Hove | V | Old Cranleighans | ||
| 20 January 2024 | Old Cranleighans | V | Old Walcountians | ||
| 27 January 2024 | Twickenham | V | Old Cranleighans | ||
| 3 February 2024 | Old Cranleighans | V | East Grinstead | ||
| 17 February 2024 | Trinity | V | Old Cranleighans | ||
| 2 March 2024 | Old Cranleighans | V | Teddington | ||
| 16 March 2024 | KCS Old Boys | V | Old Cranleighans | ||
| 23 March 2024 | Old Cranleighans | V | Eastbourne | ||
| 6 April 2024 | Old Cranleighans | V | Old Tiffinians |
View the 1st XV league table on the England Rugby website.
2nd XV
| 16 September 2023 | Old Cranleighan 2nd XV | V | Sutton & Epsom 4th XV Dev | L | AWO |
| 23 September 2023 | Old Emanuel 2nd XV | V | Old Cranleighan 2nd XV | L | HWO |
| 30 September 2023 | Old Cranleighan 2nd XV | V | Old Wimbledonians Rams | D | 20 – 20 |
| 21 October 2023 | Purley John Fisher 2nd XV | V | Old Cranleighan 2nd XV | ||
| 4 November 2023 | Old Cranleighan 2nd XV | V | Old Whitgiftian Wanderers | ||
| 11 November 2023 | Trinity 2nd XV | V | Old Cranleighan 2nd XV | ||
| 18 November 2023 | Old Cranleighan 2nd XV | V | Battersea Ironsides 5th XV | ||
| 2 December 2023 | London Media 2nd XV | V | Old Cranleighan 2nd XV | ||
| 9 December 2023 | Old Cranleighan 2nd XV | V | Bec Old Boys 3rd XV | ||
| 13 January 2024 | Old Cranleighan 2nd XV | V | Old Emanuel 2nd XV | ||
| 20 January 2024 | Old Wimbledonians Rams | V | Old Cranleighan 2nd XV | ||
| 27 January 2024 | Old Cranleighan 2nd XV | V | Purley John Fisher 2nd XV | ||
| 3 February 2024 | Old Whitgiftian Wanderers | V | Old Cranleighan 2nd XV | ||
| 17 February 2024 | Old Cranleighan 2nd XV | V | Trinity 2nd XV | ||
| 2 March 2024 | Battersea Ironsides 5th XV | V | Old Cranleighan 2nd XV | ||
| 16 March 2024 | Old Cranleighan 2nd XV | V | London Media 2nd XV | ||
| 23 March 2024 | Bec Old Boys 3rd XV | V | Old Cranleighan 2nd XV | ||
| 6 April 2024 | Sutton & Epsom 4th XV Dev | V | Old Cranleighan 2nd XV |