Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| Challenger Anning | 2019/04/21 06:00 | Jay Clarke v Prajnesh Gunneswaran | 6-4,6-3 |
| ATP Miami | 2019/03/20 16:45 | Prajnesh Gunneswaran v Jay Clarke | 6-4,6-4 |
| Challenger Andria | 2022/11/21 18:45 | Ryan Peniston v Jay Clarke | 6-2,6-1 |
| Challenger Helsinki | 2022/11/14 15:25 | Jay Clarke v Adrian Andreev | 1-6,6-3,6-7 |
| Challenger Roanne | 2022/11/09 12:40 | Jay Clarke v Nikolas Sanchez Izquierdo | 3-6,6-1,2-6 |
| Challenger Seoul | 2022/10/11 07:35 | Jay Clarke v Kamil Majchrzak | 2-6,2-6 |
| Challenger Gwangju | 2022/10/04 10:10 | Uisung Park v Jay Clarke | 6-3,3-6,6-2 |
| Challenger Cassis | 2022/09/06 12:00 | Laurent Lokoli v Jay Clarke | 6-3,7-5 |
| Challenger Mallorca | 2022/09/02 20:35 | Zizou Bergs v Jay Clarke | 6-3,6-2 |
| Challenger Mallorca | 2022/09/01 14:00 | Antoine Bellier v Jay Clarke | 4-6,4-6 |
| Challenger Yokkaichi | 2022/11/22 05:15 | Kaichi Uchida v Prajnesh Gunneswaran | 6-3,1-6,6-3 |
| Challenger Champaign | 2022/11/18 17:00 | Prajnesh Gunneswaran v Ben Shelton | 3-6,5-7 |
| Challenger Champaign | 2022/11/16 17:25 | Prajnesh Gunneswaran v Sebastian Fanselow | 3-6,6-2,7-5 |
| Challenger Champaign | 2022/11/14 22:55 | Stefan Kozlov v Prajnesh Gunneswaran | 6-3,3-6,4-6 |
| Challenger Knoxville | 2022/11/09 22:20 | Prajnesh Gunneswaran v Stefan Kozlov | 4-6,3-6 |
| Challenger Knoxville | 2022/11/08 19:50 | Prajnesh Gunneswaran v Blaise Bicknell | 6-1,6-2 |
| Challenger Sydney | 2022/11/01 04:05 | Prajnesh Gunneswaran v Max Purcell | 6-4,6-7,6-7 |
| Challenger Playford | 2022/10/25 06:05 | Prajnesh Gunneswaran v James Duckworth | 5-7,1-6 |