| Date | Division | Match | String | Opponent | Result |
| 09/10/2019 | Division 3 | Radlett 2 v Haileybury 1 | 3 | Isaac Green | Lost 0-3 |
| 10/10/2019 | Division 4 | Haileybury 2 v Active Fitness 2 | 2 | Dominic Webster | Won 3-1 |
| 15/10/2019 | Division 5 | Haileybury 3 v Chantry 1 | 1 | Mark Douglas | Won 3-1 |
| 17/10/2019 | Division 4 | Allenburys 1 v Haileybury 2 | 2 | Cesar Ramirez-Molina | Won 3-0 |
| 07/11/2019 | Division 4 | Haileybury 2 v Ickleford 1 | 2 | Kevin Waring | Won 3-2 |
| 14/11/2019 | Division 4 | Nuffield 4 v Haileybury 2 | 2 | Joel Burnham | Won 3-2 |
| 21/11/2019 | Division 4 | Haileybury 2 v Harpenden 4 | 1 | Laurence Cross | Won 3-1 |
| 28/11/2019 | Division 4 | Radlett 3 v Haileybury 2 | 2 | Daniel Wolfson | Won 3-0 |
| 12/12/2019 | Division 4 | Haileybury 2 v Letchworth 2 | 2 | Jason Gollaglee | Lost 2-3 |
| 16/01/2020 | Division 4 | Active Fitness 2 v Haileybury 2 | 1 | Salvador Myro | Lost 1-3 |
| 23/01/2020 | Division 4 | Haileybury 2 v Allenburys 1 | 1 | Max Tetlow | Lost 0-3 |
| 30/01/2020 | Division 4 | Ickleford 1 v Haileybury 2 | 1 | Tom Archer | Lost 1-3 |
| 06/02/2020 | Division 4 | Haileybury 2 v Nuffield 4 | 1 | Rob Weeks | Won 3-1 |
| 27/02/2020 | Division 4 | Haileybury 2 v Radlett 3 | 1 | Steve Hambling | Won 3-1 |
| 12/03/2020 | Division 4 | Letchworth 2 v Haileybury 2 | 1 | Jason Gollaglee | Lost 0-3 |
