Stadium: Court 1 - Indoor Round: 25 Ground: Hardcourt outdoor
| ITF M15 Tacarigua | 2023/04/20 18:00 | Edward Winter v Finn Reynolds | 5-7,6-2,7-6 |
| ITF M15 Tacarigua | 2023/04/18 21:00 | Finn Reynolds v Joseph Cadogan | 6-4,7-5 |
| ITF M15 Tacarigua | 2023/04/17 18:00 | Finn Reynolds v Chukwudumebi Smarty | 6-2,6-1 |
| ITF M25 Calabasas | 2023/03/23 20:45 | Omni Kumar v Finn Reynolds | 6-4,3-6,10-2 |
| ITF M25 Calabasas | 2023/03/21 20:55 | Federico Agustin Gomez v Finn Reynolds | 6-1,3-6,9-11 |
| ITF M25 Calabasas | 2023/03/20 18:00 | Joe Tyler v Finn Reynolds | 1-6,6-4,3-10 |
| ITF M25 Bakersfield | 2023/03/16 02:40 | Alex Michelsen v Finn Reynolds | 6-3,6-2 |
| ITF M25 Bakersfield | 2023/03/15 19:00 | Finn Reynolds v Toby Martin | 6-4,6-7,10-7 |
| ITF M15 Tacarigua | 2023/04/20 20:05 | Maxence Broville v Justin Roberts | 5-7,6-2,6-1 |
| ITF M15 Tacarigua | 2023/04/18 23:20 | Justin Roberts v Joshua Sheehy | 6-2,7-6 |
| ITF M25 Santo Domingo | 2023/02/25 14:50 | Alex Bolt v Justin Roberts | 6-4,6-3 |
| ITF M25 Santo Domingo | 2023/02/24 17:30 | Justin Roberts v Roberto Cid Subervi | 6-3,2-6,6-2 |
| ITF M25 Santo Domingo | 2023/02/23 14:00 | Alvaro Lopez San Martin v Justin Roberts | 4-6,5-7 |
| ITF M25 Santo Domingo | 2023/02/21 17:45 | Justin Roberts v Miguel Damas | 6-3,2-6,7-6 |
| ITF M25 Santo Domingo | 2023/02/15 15:25 | Justin Roberts v Jorge Panta | 2-6,4-6 |
| ITF M25 Santo Domingo | 2023/02/14 13:00 | Justin Roberts v Graham Maassen | 6-1,2-6,11-9 |