Stadium: Cancha 3 Round: 25 Ground: Clay
| Challenger Drummondville | 2023/11/15 18:05 | Michael Vrbensky v Liam Draxl | 6-7,6-3,7-5 |
| Challenger Drummondville | 2023/11/14 23:30 | Steven Diez v Liam Draxl | 4-6,7-6,1-6 |
| Challenger Calgary | 2023/11/12 22:55 | Dominik Koepfer v Liam Draxl | 4-6,3-6 |
| Challenger Calgary | 2023/11/11 21:10 | Andres Martin v Liam Draxl | 6-7,7-5,3-6 |
| Challenger Calgary | 2023/11/10 22:00 | Liam Draxl v Inaki Montes-De La Torre | 7-5,5-7,6-1 |
| Challenger Calgary | 2023/11/08 17:00 | Liam Draxl v Luke Saville | 6-1,6-2 |
| Challenger Calgary | 2023/11/06 21:00 | Kimmer Coppejans v Liam Draxl | 4-6,1-6 |
| ITF - Edmonton M25 | 2023/11/04 19:50 | Justin Boulais v Liam Draxl | 6-4,6-1 |
| Challenger Montevideo | 2023/11/14 15:00 | Murkel Dellien v Thiago Monteiro | 0-6,4-6 |
| Challenger Montevideo | 2023/11/13 15:00 | Murkel Dellien v Gerard Campana Lee | 6-2,6-3 |
| Challenger Montevideo | 2023/11/12 16:45 | Murkel Dellien v Wilson Leite | 6-1,6-3 |
| Challenger Lima | 2023/11/06 16:00 | Murkel Dellien v Alvaro G Meza | 7-5,2-6,3-6 |
| Challenger Lima | 2023/11/05 15:00 | Murkel Dellien v Rodrigo Varillas | 6-0,6-1 |
| Challenger Guayaquil | 2023/10/31 19:00 | Murkel Dellien v Facundo Diaz Acosta | 3-6,2-6 |
| Challenger Curitiba | 2023/10/24 17:15 | Orlando Luz v Murkel Dellien | 6-1,7-5 |
| Challenger Buenos Aires | 2023/10/10 16:35 | Murkel Dellien v Mariano Navone | 2-6,2-6 |