| Date | Division | Match | String | Opponent | Result |
| 22/09/2022 | Division 4 South West | Hilbre Squash Club 1 v Heswall 5 | 1 | Barry Downey | Lost 0-3 |
| 29/09/2022 | Division 4 South West | Heswall 5 v Brook Hotels 1 | 2 | Mike Tilling | Won 3-2 |
| 06/10/2022 | Division 4 South West | Tattenhall 3 v Heswall 5 | 1 | Tim Salt | Won 3-0 |
| 13/10/2022 | Division 4 South West | Heswall 5 v Warrington 6 | 1 | Peter Smallshaw | Won 3-0 |
| 20/10/2022 | Division 4 South West | Whitby 1 v Heswall 5 | 1 | Mark Griffiths | Lost 2-3 |
| 03/11/2022 | Division 4 South West | Heswall 5 v Holywell Leisure SC 2 | 2 | Chris Bunnell | Won 3-0 |
| 10/11/2022 | Division 4 South West | Mollington Banastre 1 v Heswall 5 | 1 | James Kalahar | Lost 2-3 |
| 17/11/2022 | Division 4 South West | Heswall 5 v Neston 4 | 1 | Andy Watson | Lost 1-3 |
| 01/12/2022 | Division 4 South West | Heswall 5 v Chester Rugby 3 | 1 | Matt Kearney | Lost 1-3 |
| 08/12/2022 | Division 4 South West | Heswall 4 v Heswall 5 | 1 | Simon Malcolm | Lost 1-3 |
| 15/12/2022 | Division 4 South West | Heswall 5 v New Brighton 1 | 1 | Karl Mullins | Lost 0-3 |
| 12/01/2023 | Division 4 South West | Heswall 5 v Hilbre Squash Club 1 | 1 | Barry Downey | Won 3-0 |
| 19/01/2023 | Division 4 South West | Brook Hotels 1 v Heswall 5 | 1 | Jamie Robertson | Lost 0-3 |
| 26/01/2023 | Division 4 South West | Heswall 5 v Tattenhall 3 | 1 | Paul Williams | Lost 0-3 |
| 02/02/2023 | Division 4 South West | Warrington 6 v Heswall 5 | 1 | Peter Smallshaw | Won 3-1 |
| 23/02/2023 | Division 4 South West | Heswall 5 v Moss Farm 1 | 1 | Paul Smith | Lost 1-3 |
| 02/03/2023 | Division 4 South West | Holywell Leisure SC 2 v Heswall 5 | 1 | Michael Plumb | Lost 2-3 |
| 09/03/2023 | Division 4 South West | Heswall 5 v Mollington Banastre 1 | 2 | Nathan Delves | Lost 0-3 |
| 16/03/2023 | Division 4 South West | Neston 4 v Heswall 5 | 2 | Darren Reid | Won 3-1 |
| 30/03/2023 | Division 4 South West | Chester Rugby 3 v Heswall 5 | 1 | Tom O'Brien | Lost 1-3 |
| 20/04/2023 | Division 4 South West | Heswall 5 v Heswall 4 | 2 | Matthew Cliff | Lost 0-3 |
| 27/04/2023 | Division 4 South West | New Brighton 1 v Heswall 5 | 2 | Karl Mullins | Lost 0-3 |
