Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| Challenger Savannah | 2023/04/24 18:45 | Alex Michelsen v Patrick Kypson | 6-4,3-6,6-7 |
| Challenger Tallahassee | 2023/04/21 19:55 | Enzo Couacaud v Alex Michelsen | 7-5,7-5 |
| Challenger Tallahassee | 2023/04/20 16:30 | Lucas Pouille v Alex Michelsen | 3-6,5-7 |
| Challenger Tallahassee | 2023/04/18 15:00 | Alex Michelsen v Camilo Ugo Carabelli | 5-7,6-3,6-2 |
| ITF M25 Calabasas | 2023/03/26 19:30 | Alex Michelsen v Nathan Ponwith | 3-6,7-6,5-7 |
| ITF M25 Calabasas | 2023/03/25 19:50 | Alex Michelsen v Luke Saville | 6-2,6-1 |
| ITF M25 Calabasas | 2023/03/24 16:55 | Alex Michelsen v Kris Van Wyk | 7-5,7-6 |
| ITF M25 Calabasas | 2023/03/23 22:20 | Alex Michelsen v Murphy Cassone | 6-4,6-4 |
| ATP Geneva | 2023/05/20 11:30 | Alessandro Giannessi v Denis Yevseyev | 3-6,6-4,6-2 |
| Challenger Oeiras | 2023/05/14 15:30 | Daniel Rodrigues v Denis Yevseyev | 6-4,2-6,6-4 |
| Challenger Prague Qual | 2023/05/07 08:30 | Denis Yevseyev v Martin Damm | 3-6,2-6 |
| Challenger Prague | 2023/04/30 14:45 | Federico Gaio v Denis Yevseyev | 6-0,6-7,6-3 |
| Challenger Savannah | 2023/04/25 14:00 | Martin Damm v Denis Yevseyev | 6-1,6-4 |
| Challenger Morelos | 2023/04/19 18:10 | Mark Lajal v Denis Yevseyev | 7-5,6-1 |
| Challenger Morelos | 2023/04/18 16:30 | Naoki Nakagawa v Denis Yevseyev | 6-7,6-4,2-6 |
| Challenger Leon | 2023/04/11 21:05 | Denis Yevseyev v Benjamin Lock | 5-7,5-7 |