Stadium: Court 5 Round: 27 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2021/05/19 08:30 | Roy Smith v Maxence Beauge | 6-4,2-6,7-6 |
| ITF M15 Monastir | 2021/05/12 09:55 | Uisung Park v Roy Smith | 6-2,6-1 |
| Challenger Salinas | 2021/04/18 15:00 | Roy Smith v Nicolas Mejia | 4-6,4-6 |
| Challenger Orlando | 2021/04/12 14:00 | Roberto Quiroz v Roy Smith | 6-4,2-6,6-2 |
| Challenger Cleveland | 2021/03/17 16:20 | Aleksandar Kovacevic v Roy Smith | 7-6,6-3 |
| Challenger Cleveland | 2021/03/16 19:10 | Nick Chappell v Roy Smith | 4-6,7-5,4-6 |
| ITF M15 Nur-Sultan | 2021/02/11 08:15 | Roy Smith v Mats Rosenkranz | 6-3,4-6,5-7 |
| ITF M15 Nur-Sultan | 2021/02/10 03:55 | Roy Smith v Marco Brugnerotto | 6-4,6-7,6-3 |
| ITF M15 Monastir | 2021/05/20 08:20 | Thomas Fancutt v Michail Pervolarakis | 6-4,7-5 |
| ITF M15 Monastir | 2021/05/18 08:30 | Thomas Fancutt v Guido Ivan Justo | 6-2,6-4 |
| ITF M15 Monastir | 2021/05/13 10:20 | Thomas Fancutt v Antoine Bellier | 2-6,6-7 |
| ITF M15 Monastir | 2021/05/12 08:30 | Thomas Fancutt v Tomas Farjat | 6-3,6-4 |
| UTR Pro Tennis Series Brisbane | 2021/03/06 02:00 | Calum Puttergill v Thomas Fancutt | 7-6,6-3 |
| UTR Pro Tennis Series Brisbane | 2021/03/05 00:30 | Thomas Fancutt v Arjun Mehrotra | 6-4,6-4 |
| UTR Pro Tennis Series Brisbane | 2021/03/03 03:00 | Thomas Fancutt v Omar Jasika | 3-6,7-5,3-6 |
| UTR Pro Tennis Series Brisbane | 2021/03/02 03:30 | Thomas Fancutt v Moerani Bouzige | 6-4,4-6,6-4 |