| Alistair Compton | L | 2023-10-18 | Maidstone 2 v Rainham (Kent) 2 | MID Stevenson Cup |
| Henry Cove | L | 2023-10-25 | Maidstone 3 v Hastings & St Leonards 2 | MID En Passant Cup |
| Lasitha Yasanga Herath | L | 2023-11-01 | Maidstone 4 v Medway 2 | MID Harvey Cup |
| Mark D Brougham | L | 2023-11-12 | Hastings & St Leonards 1 v Maidstone 2 | MID Stevenson Cup |
| Aram Swiatkowski | L | 2023-11-15 | Medway 1 v Maidstone 3 | MID En Passant Cup |
| Max Garnero | D | 2023-11-27 | Weald of Kent 1 v Maidstone 3 | MID En Passant Cup |
| James M Wheeler | D | 2023-12-03 | Hastings & St Leonards 3 v Maidstone 4 | MID Harvey Cup |
| Robert Springett | W | 2023-12-13 | Rainham (Kent) 2 v Maidstone 2 | MID Stevenson Cup |
| Paul Jeffery | D | 2024-01-24 | Maidstone 3 v Medway 1 | MID En Passant Cup |
| Robert Jacobs | D | 2024-01-29 | Tunbridge Wells 1 v Maidstone 2 | MID Stevenson Cup |
| Kristof Siklodi | L | 2024-01-31 | Maidstone 3 v Swale 1 | MID En Passant Cup |
| Tobias W Stock | L | 2024-02-07 | Maidstone 1 v Rainham (Kent) 1 | MID County / Lewis Cup |
| Henry Cove | D | 2024-02-18 | Hastings & St Leonards 2 v Maidstone 3 | MID En Passant Cup |
| Chris D Brown | W | 2024-02-28 | Rainham (Kent) 3 v Maidstone 4 | MID Harvey Cup |
| Tobias W Stock | D | 2024-03-06 | Maidstone 1 v Rainham (Kent) 1 | MID County / Lewis Cup |
| Tobias W Stock | D | 2024-03-27 | Rainham (Kent) 1 v Maidstone 1 | MID County / Lewis Cup |
| Ben Fearnley-Sander | L | 2024-04-24 | Maidstone 2 v Charlton 2 | Stevenson Cup Semi Final |
