Stadium: Court 9 Round: 14 Ground: Hardcourt indoor
| Challenger Las Vegas | 2021/10/25 22:30 | Michael Mmoh v Nick Chappell | 6-2,6-1 |
| Challenger Las Vegas | 2021/10/25 18:00 | Nick Chappell v Shintaro Mochizuki | 7-5,2-6,2-6 |
| Challenger Las Vegas | 2021/10/24 17:00 | Nick Chappell v Roy Smith | 7-6,6-7,6-2 |
| Challenger Santiago | 2021/10/11 17:15 | Nick Chappell v Hernan Casanova | 3-6,4-6 |
| Challenger Santiago | 2021/10/06 16:00 | Nick Chappell v Sebastian Baez | 7-5,4-6,1-6 |
| Challenger Santiago | 2021/10/04 22:55 | Diego F Flores v Nick Chappell | 3-6,6-3,5-7 |
| Challenger Istanbul | 2021/09/14 11:15 | Alexandre Muller v Nick Chappell | 6-4,6-2 |
| Challenger Istanbul | 2021/09/13 07:30 | Nick Chappell v Alexander Shevchenko | 6-4,6-2 |
| ITF M15 Fayetteville | 2021/09/22 20:10 | Gianni Ross v Paul Jubb | 6-4,4-6,2-6 |
| ITF M25 Fayetteville | 2021/09/21 14:00 | Charles Broom v Gianni Ross | 3-6,3-6 |
| ITF M15 Gdyně | 2021/08/09 08:00 | Gianni Ross v Filip Kolasinski | 7-6,1-6,9-11 |
| ITF M15 Gdyně | 2021/08/08 08:00 | Francisco Vittar v Gianni Ross | 2-6,6-0,7-10 |
| ITF M15 Frederiksberg | 2021/08/03 12:45 | Oscar Moraing v Gianni Ross | 7-5,4-6,6-4 |
| ITF M15 Frederiksberg | 2021/08/03 11:30 | Oscar Moraing v Gianni Ross | 7-5,4-6,6-4 |
| ITF M15 Frederiksberg | 2021/08/02 11:25 | Gianni Ross v Bjorn Nareyka | 6-2,6-0 |
| ITF M15 Frederiksberg | 2021/08/01 08:00 | Gianni Ross v Raphael Calzi | 7-5,6-4 |