Stadium: Court 3 Round: 14 Ground: Hardcourt outdoor
| Toronto, Canada | 2023/08/05 18:10 | Marcos Giron v Nick Chappell | 6-4,3-6,6-2 |
| ATP - Los Cabos | 2023/07/30 02:30 | Abedallah Shelbayh v Nick Chappell | 6-3,6-2 |
| Challenger Granby | 2023/07/18 23:40 | Nick Chappell v Thai-Son Kwiatkowski | 5-7,3-6 |
| Challenger Granby | 2023/07/17 16:05 | Nick Chappell v Cozbinov, Alexander | 7-6,0-6,7-6 |
| Challenger Granby | 2023/07/16 21:20 | Nick Chappell v Keegan Rice | 6-1,6-3 |
| Dallas, Singles Main, M-ITF-USA-18A | 2023/07/11 21:30 | Alexander Bernard v Nick Chappell | 1-6,6-4,3-6 |
| Challenger Bloomfield Hills | 2023/07/03 20:55 | Boulais, Justin v Nick Chappell | 4-6,7-5,6-4 |
| ITF - M25 Santo Domingo | 2023/07/01 13:30 | Liam Draxl v Nick Chappell | 7-6,6-1 |
| Santo Domingo, Dominican Republic | 2023/08/06 17:00 | Juan Sebastian Gomez v James Tracy | 7-5,6-3 |
| ITF M25 Laval | 2023/07/16 16:00 | James Tracy v Blaise Bicknell | 6-3,3-6,4-6 |
| ITF M25 Laval | 2023/07/15 13:55 | James Tracy v Leo Vithoontien | 6-3,6-2 |
| ITF M25 Laval | 2023/07/14 17:55 | Alafia Ayeni v James Tracy | 3-6,7-5,1-6 |
| ITF M25 Laval | 2023/07/14 14:00 | Jaden Weekes v James Tracy | 4-6,2-6 |
| ITF M25 Laval | 2023/07/12 15:30 | Adam Faragcao v James Tracy | 3-6,3-6 |
| ITF - M25 Santo Domingo | 2023/06/30 13:30 | James Tracy v Liam Draxl | 4-6,2-6 |
| ITF - M25 Santo Domingo | 2023/06/29 15:35 | Evan Bynoe v James Tracy | 1-6,2-6 |