| Barry MS Jolly | W | 2023-10-09 | Highcliffe B v New Milton A | B&DCL Div 2 |
| Richard Ormesher | L | 2023-10-16 | Ringwood B v Highcliffe C | B&DCL Div 3 |
| Derek Mount | W | 2023-11-06 | Purbeck B v Highcliffe C | DCL Div 3 |
| Kaifer Rait-McDonald | W | 2023-11-20 | Highcliffe B v Weymouth B | DCL Div 2 |
| Michael Williams | W | 2023-11-23 | Round 2 | HCCSW |
| Ellis Fretwell | L | 2023-11-27 | Highcliffe C v Poole C | B&DCL Div 3 |
| Steve Blake | W | 2023-12-04 | Highcliffe C v Weymouth C | DCL Div 3 |
| John R Bowley | L | 2023-12-11 | Highcliffe B v Wimborne B | DCL Div 2 |
| E James Schumacher | W | 2023-12-12 | Bournemouth A v Highcliffe B | B&DCL Div 2 |
| Nathaniel J Cleland | D | 2024-01-10 | Wimborne C v Highcliffe C | B&DCL Div 3 |
| Ken Dixon | W | 2024-01-22 | Highcliffe B v Southbourne B | B&DCL Div 2 |
| Stephen Bolton | L | 2024-01-29 | Highcliffe C v Bournemouth C | B&DCL Div 3 |
| Tim Joyce | W | 2024-02-05 | Highcliffe C v Poole C | DCL Div 3 |
| Richard Ormesher | L | 2024-02-19 | Highcliffe C v Ringwood B | B&DCL Div 3 |
| John Belinger | D | 2024-02-20 | New Milton A v Highcliffe B | B&DCL Div 2 |
| Sidney A Jones | W | 2024-02-29 | Dorchester D v Highcliffe C | DCL Div 3 |
| Mike Rutter | W | 2024-03-04 | Poole B v Highcliffe B | DCL Div 2 |
| Martin O.Neill | L | 2024-03-11 | Highcliffe Carlsens v Poole The Other One | B&DCL Team Handicap Knockout Cup - 2024 |
| Peter Austin | W | 2024-03-15 | Southbourne C v Highcliffe C | B&DCL Div 3 |
| Christopher G Webb | L | 2024-03-18 | Highcliffe B v Dorchester C | DCL Div 2 |
| Ellis Fretwell | L | 2024-04-08 | Poole C v Highcliffe C | B&DCL Div 3 |
| Nicholas B Stout | W | 2024-04-15 | Highcliffe C v Purbeck B | DCL Div 3 Knockout |
| Nathaniel J Cleland | L | 2024-04-22 | Highcliffe C v Wimborne C | B&DCL Div 3 |
