| Dominik Swiatkowski | L | 2023-11-06 | Weald of Kent 1 v Medway 1 | MID En Passant Cup |
| James Williams | W | 2023-11-15 | Maidstone 8 v Weald of Kent 4 | MID Intro Cup |
| Michael Hawkes | W | 2023-11-20 | Weald of Kent 3 v Maidstone 6 | MID Tom Fuller Cup |
| Michael Ingham | D | 2023-11-23 | Swale 3 v Weald of Kent 4 | MID Intro Cup |
| Harry Homersham | D | 2023-12-06 | Maidstone 5 v Weald of Kent 3 | MID Tom Fuller Cup |
| Paul Foster | W | 2023-12-11 | Weald of Kent 2 v Medway 2 | MID Harvey Cup |
| Dominik Swiatkowski | L | 2024-01-03 | Medway 6 v Weald of Kent 4 | MID Intro Cup |
| Tye Martin | W | 2024-01-08 | Weald of Kent 4 v Maidstone 7 | MID Intro Cup |
| Gary R Clifford | W | 2024-01-10 | Rainham (Kent) 3 v Weald of Kent 2 | MID Harvey Cup |
| Joshua James Daplyn | L | 2024-01-22 | Weald of Kent 3 v Tunbridge Wells 2 | MID Tom Fuller Cup |
| Isaac Oluwole | L | 2024-01-24 | Medway 3 v Weald of Kent 3 | MID Tom Fuller Cup |
| Tom Creed | D | 2024-01-29 | Weald of Kent 1 v Swale 1 | MID En Passant Cup |
| William Walshe | D | 2024-02-05 | Weald of Kent 3 v Medway 4 | MID Tom Fuller Cup |
| Neil Miners | W | 2024-02-12 | Snodland 3 v Weald of Kent 4 | MID Intro Cup |
| Tye Martin | W | 2024-02-21 | Maidstone 4 v Weald of Kent 2 | MID Harvey Cup |
| Dimitar Milev | L | 2024-03-06 | Medway 1 v Weald of Kent 1 | MID En Passant Cup |
| Mason Woodhams | L | 2024-03-22 | Hastings & St Leonards 2 v Weald of Kent 1 | MID En Passant Cup |
| Oliver James | W | 2024-03-25 | Weald of Kent 3 v Rainham (Kent) 4 | MID Tom Fuller Cup |
| Stefan Sainiuc | L | 2024-04-03 | Maidstone 3 v Weald of Kent 1 | MID En Passant Cup |
| Derek Cosens | L | 2024-04-08 | Hastings & St Leonards 3 v Weald of Kent 2 | MID Harvey Cup |
| Nick Allen | L | 2024-04-15 | Weald of Kent 2 v Snodland 1 | MID Harvey Cup |
