Stadium: Court 2 Round: 26 Ground: Hardcourt indoor
| Challenger Rome GA | 2023/02/21 18:10 | Patrick Kypson v Keegan Smith | 6-1,7-6 |
| Challenger Rome GA | 2023/02/20 18:25 | Alex Rybakov v Patrick Kypson | 6-4,6-7,5-7 |
| Challenger Rome GA | 2023/02/19 23:45 | Keshav Chopra v Patrick Kypson | 3-6,4-6 |
| Challenger - Cleveland | 2023/01/31 16:20 | Stefan Kozlov v Patrick Kypson | 6-4,7-6 |
| ITF - M25 Wesley Chapel | 2023/01/26 16:00 | Colin Sinclair v Patrick Kypson | 6-4,6-1 |
| ITF - M25 Wesley Chapel | 2023/01/24 17:35 | Patrick Kypson v Andres Andrade | 6-0,6-2 |
| Challenger - Champaign | 2022/11/16 23:10 | Patrick Kypson v Aleksandar Vukic | 4-6,2-6 |
| Challenger - Champaign | 2022/11/15 23:40 | Patrick Kypson v Inaki Montes-De La Torre | 6-1,6-4 |
| Challenger Rome GA | 2023/02/21 15:00 | Alastair Gray v Alexis Galarneau | 6-4,6-4 |
| ITF M25 - Sheffield | 2023/01/20 10:55 | Alastair Gray v Charles Broom | 6-7,7-6,2-6 |
| ITF M25 - Sheffield | 2023/01/19 12:50 | Alastair Gray v Aidan Mchugh | 6-3,7-6 |
| ITF M25 - Sheffield | 2023/01/18 11:00 | Alastair Gray v Vito Tonejc | 6-4,6-4 |
| ITF M25 - Sheffield | 2023/01/17 12:55 | Alastair Gray v Aldin Setkic | 6-2,6-1 |
| ITF - M25 Monastir | 2022/11/24 11:05 | Dusan Obradovic v Alastair Gray | 7-5,6-7,4-6 |
| ITF - M25 Monastir | 2022/11/22 12:05 | Nicolas Philibert v Alastair Gray | 1-6,3-6 |
| ITF - M25 Sharm El Sheikh | 2022/11/17 08:00 | Alastair Gray v Amr Asrawy | 4-6,3-6 |