| Division 2 | Mon 4 Sep 2023 | #4 | Christopher Gregory (Woodfield 1) | V | Adam Bierton (Hallamshire 4) | 15-12, 15-13, 15-12 | | 3-0 |
| Division 2 | Mon 6 Nov 2023 | #3 | Christopher Gregory (Woodfield 1) | V | Albert Rutter (Abbeydale 3) | 13-15, 15-4, 11-15, 15-6, 15-7 | | 3-2 |
| Division 2 | Sun 26 Nov 2023 | #2 | Mark Campbell (Hallamshire 3) | V | Christopher Gregory (Woodfield 1) | 10-15, 15-10, 15-17, 15-13, 12-15 | | 2-3 |
| Division 2 | Mon 22 Jan 2024 | #3 | Simon Clarke (Barnsley 1) | V | Christopher Gregory (Woodfield 1) | 15-11, 15-13, 7-15, 4-15, 15-11 | | 3-2 |
| Division 2 | Mon 12 Feb 2024 | #4 | Christopher Gregory (Woodfield 1) | V | Adam Brass (Fulwood 4) | 10-15, 13-15, 15-9, 15-7, 12-15 | | 2-3 |
| Division 2 | Thu 29 Feb 2024 | #3 | Rebecca Wright (Abbeydale 3) | V | Christopher Gregory (Woodfield 1) | 11-15, 18-16, 16-14, 10-15, 15-12 | | 3-2 |
| Division 2 | Tue 5 Mar 2024 | #3 | Tom Clarke (Fulwood 3) | V | Christopher Gregory (Woodfield 1) | 10-15, 8-15, 15-8, 15-12, 12-15 | | 2-3 |
