| Date | Division | Match | String | Opponent | Result |
| 02/10/2019 | Premier | Hallamshire 2 v Barnsley 1 | 1 | Miles Jenkins | Won 3-1 |
| 09/10/2019 | Premier | Chapel Allerton 1 v Hallamshire 2 | 1 | Owain Taylor | Won 3-2 |
| 23/10/2019 | Premier | Abbeydale 1 v Hallamshire 2 | 1 | Adam Auckland | Lost 0-3 |
| 30/10/2019 | Premier | Hallamshire 2 v Woodfield Squash 1 | 1 | George Parker | Lost 0-3 |
| 06/11/2019 | Premier | Ferriby Hall 1 v Hallamshire 2 | 1 | Ben Smith | Won 3-2 |
| 13/11/2019 | Premier | Hallamshire 2 v Chapel Allerton 2 | 1 | Declan Christie | Won 3-2 |
| 04/12/2019 | Premier | Hallamshire 2 v Pontefract 1 | 1 | Lewis Doughty | Won 3-1 |
| 11/12/2019 | Premier | Dunnington 1 v Hallamshire 2 | 1 | Chris Simpson | Lost 1-3 |
| 18/12/2019 | Premier | Hallamshire 2 v Hallamshire 1 | 1 | Nick Wall | Lost 2-3 |
| 15/01/2020 | Premier | Barnsley 1 v Hallamshire 2 | 1 | Lewis Walters | Won 3-0 |
| 22/01/2020 | Premier | Hallamshire 2 v Chapel Allerton 1 | 1 | Greg Lobban | Lost 0-3 |
| 31/01/2020 | Premier | Hallamshire 1 v Hallamshire 2 | 1 | Alex Cutts | Won 3-0 |
| 05/02/2020 | Premier | Hallamshire 2 v Abbeydale 1 | 1 | Adam Auckland | Won 3-1 |
| 04/03/2020 | Premier | Chapel Allerton 2 v Hallamshire 2 | 1 | Declan Christie | Won 3-0 |
| 11/03/2020 | Premier | Hallamshire 2 v Pontefract 2 | 1 | Adam Taylor | Won 3-2 |
