| Keith Nevols | D | 2023-10-18 | Maidstone 2 v Rainham (Kent) 2 | MID Stevenson Cup |
| James M Wheeler | L | 2023-10-25 | Maidstone 3 v Hastings & St Leonards 2 | MID En Passant Cup |
| Adrian Cload | W | 2023-11-12 | Hastings & St Leonards 1 v Maidstone 2 | MID Stevenson Cup |
| Paul Jeffery | D | 2023-11-15 | Medway 1 v Maidstone 3 | MID En Passant Cup |
| Adam Dakin | L | 2023-11-27 | Weald of Kent 1 v Maidstone 3 | MID En Passant Cup |
| Rasa Norinkeviciute | L | 2023-12-03 | Hastings & St Leonards 3 v Maidstone 4 | MID Harvey Cup |
| Chris D Brown | W | 2023-12-13 | Rainham (Kent) 2 v Maidstone 2 | MID Stevenson Cup |
| David A Page | D | 2024-01-11 | Swale 1 v Maidstone 3 | MID En Passant Cup |
| Aram Swiatkowski | D | 2024-01-24 | Maidstone 3 v Medway 1 | MID En Passant Cup |
| Fred Fang | L | 2024-01-29 | Tunbridge Wells 1 v Maidstone 2 | MID Stevenson Cup |
| James M Wheeler | D | 2024-02-18 | Hastings & St Leonards 2 v Maidstone 3 | MID En Passant Cup |
| Robert Springett | L | 2024-02-28 | Rainham (Kent) 3 v Maidstone 4 | MID Harvey Cup |
| Keith Nevols | D | 2024-03-06 | Maidstone 1 v Rainham (Kent) 1 | MID County / Lewis Cup |
| Fred Fang | D | 2024-03-13 | Maidstone 2 v Tunbridge Wells 1 | MID Stevenson Cup |
| Keith Nevols | L | 2024-03-27 | Rainham (Kent) 1 v Maidstone 1 | MID County / Lewis Cup |
| Jon Cave | D | 2024-04-24 | Maidstone 2 v Charlton 2 | Stevenson Cup Semi Final |
