| Ken Smith | L | 2023-11-22 | Round 1 | HCCSW |
| Greg C Webb | L | 2023-10-09 | Highcliffe D v Wimborne E | B&DCL Div 5 |
| Tony Sanderson | L | 2023-10-30 | Poole F v Highcliffe D | B&DCL Div 5 |
| Azhar Ghose | W | 2023-11-21 | Bournemouth F v Highcliffe D | B&DCL Div 5 |
| Dan Ursell | W | 2023-11-23 | Round 2 | HCCSW |
| Tim Rushworth | L | 2023-11-27 | Highcliffe Castles v Ringwood Waifs & Strays | Bacchus |
| Barry MS Jolly | W | 2023-12-11 | Highcliffe D v New Milton B | B&DCL Div 5 |
| Tim Joyce | L | 2024-01-22 | Highcliffe D v Poole E | B&DCL Div 5 |
| Robert M Willington | L | 2024-01-29 | Highcliffe C v Bournemouth C | B&DCL Div 3 |
| Susan Kageler | W | 2024-02-02 | Round 3 | HCCSW |
| Andre F Mills | W | 2024-02-14 | Wimborne E v Highcliffe D | B&DCL Div 5 |
| Dragos Milea | W | 2024-03-04 | Highcliffe D v Poole F | B&DCL Div 5 |
| Ken MacAlaster | W | 2024-03-08 | Southbourne Seagulls v Highcliffe Fischers | B&DCL Team Handicap Knockout Cup - 2024 |
| Azhar Ghose | L | 2024-03-18 | Highcliffe D v Bournemouth F | B&DCL Div 5 |
| Chris Foley | D | 2024-05-17 | Southbourne Seagulls v Highcliffe Castles | Bacchus |
| Ken Dixon | W | 2024-06-17 | Highcliffe v Southbourne | B&DCL Summer League - 2024 |
| Bailey Brown | W | 2024-06-26 | Poole v Highcliffe | B&DCL Summer League - 2024 |
| Ron Salinger | W | 2024-07-01 | Highcliffe v Wimborne | B&DCL Summer League - 2024 |
