Stadium: Cancha Central Round: 25 Ground: Clay
| 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 |
| ITF M15 Concepcion | 2023/12/12 17:35 | Nicolas Villalon v Paulo A S Dos Santos | 2-6,6-7 |
| ITF M15 Concepcion | 2023/12/11 13:00 | Nicolas Villalon v Miguel Angel Cabrera | 6-3,3-6,10-7 |
| ITF M15 Concepcion | 2023/12/10 13:00 | Nicolas Villalon v Hans Albert Schubert | 2-6,7-5,10-4 |
| ITF M15 Concepcion | 2023/12/05 14:00 | Gonzalo Villanueva v Nicolas Villalon | 6-1,6-3 |
| Challenger Temuco | 2023/11/26 15:10 | Andres Andrade v Nicolas Villalon | 1-6,6-0,6-4 |
| ITF M15 Santa Cruz | 2023/11/21 23:00 | Nicolas Villalon v Juan Carlos Prado Angelo | 6-4,3-6,0-6 |
| ITF M15 Santa Cruz | 2023/11/20 22:05 | Nicolas Villalon v Thiago Cigarran | 1-6,6-4,10-3 |
| ITF M15 Santa Cruz | 2023/11/19 17:30 | Nicolas Villalon v Gino Romano | 6-3,7-5 |