Stadium: Court 8 Round: 54 Ground: Clay
| UTR Pro Tennis Series Florida | 2021/01/14 14:00 | Matthew Segura v Drew Van Orderlain | 4-6,6-4,5-3 |
| ITF M15 Boca Raton | 2023/11/17 18:00 | Matthew Segura v Arvid Nordquist | 4-6,3-6 |
| ITF M15 Boca Raton | 2023/11/17 14:00 | Matthew Segura v Martin Katz | 7-5,7-5 |
| ITF M15 Tallahassee | 2023/10/25 18:30 | Felix Corwin v Matthew Segura | 6-2,6-4 |
| UTR Pro Atlanta | 2023/06/13 17:10 | Matthew Segura v Corey Craig | 3-6,1-6 |
| UTR Pro Atlanta | 2023/06/12 21:52 | Matthew Segura v Michael Ross | 4-6,4-6 |
| UTR Pro Florida | 2023/05/28 16:33 | Jamie Connel v Matthew Segura | 4-6,7-6,6-0 |
| UTR Pro Florida | 2023/05/27 18:30 | Isaac Nortey v Matthew Segura | 5-7,4-6 |
| UTR Pro Florida | 2023/05/26 19:50 | Matthew Segura v Noureldin Adam | 6-0,3-6,6-3 |
| Challenger Calgary | 2023/11/05 19:55 | Drew Van Orderlain v Ryan Seggerman | 4-6,4-6 |
| ITF M25 Edmonton | 2023/10/31 17:20 | Nicolas Kotzen v Drew Van Orderlain | 6-2,6-4 |
| ITF M25 Edmonton | 2023/10/30 18:55 | Drew Van Orderlain v Frederick McRae | 6-0,6-0 |
| ITF M25 Edmonton | 2023/10/29 18:10 | Drew Van Orderlain v Igor Danich | 4-6,6-3,10-3 |
| ITF M25 Saint-Augustin | 2023/10/25 18:25 | Drew Van Orderlain v Junghee You | 4-6,6-1,5-7 |
| ITF M25 Saint-Augustin | 2023/10/24 14:00 | Drew Van Orderlain v Henry Lieberman | 6-4,7-6 |
| ITF M25 Saint-Augustin | 2023/10/23 14:00 | Drew Van Orderlain v Tom Dynka | 6-0,6-0 |
| ITF M15 Morelia | 2023/10/18 19:00 | Felix Corwin v Drew Van Orderlain | 6-4,6-2 |