| Date | Division | Match | String | Opponent | Result |
| 18/10/2023 | Division 5 | Tunbridge Wells SRC 4 v Maidstone 2 | 3 | Edward Wales | Lost 1-3 |
| 24/10/2023 | Division 5 | Maidstone 2 v Poult Wood 4 | 4 | Darren Nott | Won 3-0 |
| 01/11/2023 | Division 5 | Warlingham 1 v Maidstone 2 | 2 | Hamish Russell | Lost 0-3 |
| 07/11/2023 | Division 5 | Maidstone 2 v Parklangley 3 | 3 | Simon Atkinson | Won 3-2 |
| 16/11/2023 | Division 5 | Knole Park 2 v Maidstone 2 | 4 | Tim Handel | Won 3-1 |
| 21/11/2023 | Division 5 | Maidstone 2 v Waterfront 2 | 4 | Luca Brutti | Won 3-0 |
| 29/11/2023 | Division 5 | Sundridge Park 3 v Maidstone 2 | 3 | Emre Heatherwick | Won 3-0 |
| 05/12/2023 | Division 5 | Maidstone 2 v Bexley 5 | 3 | Steve Tucker | Won 3-2 |
| 14/12/2023 | Division 5 | Wells Squash Club 2 v Maidstone 2 | 3 | Nick Hughes | Lost 2-3 |
| 19/12/2023 | Division 4 | Parklangley 2 v Maidstone 1 | 3 | Gerald Tredinnick | Lost 0-3 |
| 16/01/2024 | Division 5 | Maidstone 2 v Tunbridge Wells SRC 4 | 3 | Edward Wales | Lost 1-3 |
| 23/01/2024 | Division 5 | Poult Wood 4 v Maidstone 2 | 3 | Jake Wallis | Lost 2-3 |
| 06/02/2024 | Division 5 | Maidstone 2 v Warlingham 1 | 3 | Billy Hick | Won 3-0 |
| 05/03/2024 | Division 5 | Waterfront 2 v Maidstone 2 | 3 | Ashley Scott | Lost 1-3 |
| 12/03/2024 | Division 5 | Maidstone 2 v Sundridge Park 3 | 3 | Catherine Cole | Won 3-0 |
| 21/03/2024 | Division 5 | Bexley 5 v Maidstone 2 | 3 | Adam Friswell | Won 3-1 |
| 02/04/2024 | Division 5 | Maidstone 2 v Wells Squash Club 2 | 4 | Alex Smith | Won 3-0 |
| 09/04/2024 | Division 5 | Maidstone 2 v Knole Park 2 | 3 | Tim Handel | Won 3-0 |
