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 - Sunrise | 2024/02/05 15:00 | Matthew Segura v Obrad Markovski | 6-3,6-4 |
| ITF M25 - Wesley Chapel | 2024/01/23 13:45 | Kyle Overmyer v Matthew Segura | 6-3,6-0 |
| 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 |
| ITF M15 - Sunrise | 2024/02/05 15:00 | Drew Van Orderlain v Mwendwa Mbithi | 4-6,7-5,10-3 |
| ITF M25 - Wesley Chapel | 2024/01/22 14:00 | Trey Hilderbrand v Drew Van Orderlain | 6-4,6-3 |
| ITF M25 - Ithaca | 2024/01/17 17:00 | Henrik Wiersholm v Drew Van Orderlain | 6-3,6-2 |
| ITF M25 - Ithaca | 2024/01/16 15:30 | Noah Eisenberg v Drew Van Orderlain | 1-6,0-6 |
| ITF M25 - Ithaca | 2024/01/15 15:00 | Jack McCarthy v Drew Van Orderlain | 4-6,2-6 |
| 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 |