Stadium: Court 9 Round: 25 Ground: Clay
| Challenger Orlando | 2021/06/06 14:00 | Ryan Harrison v Nick Chappell | 2-6,6-7 |
| Challenger Little Rock | 2021/05/31 21:00 | Goncalo Oliveira v Ryan Harrison | 7-5,7-6 |
| Challenger Tallahassee | 2021/04/21 19:00 | Ryan Harrison v Michael Mmoh | 4-6,3-6 |
| Challenger Tallahassee | 2021/04/20 14:00 | Ryan Harrison v Donald Young | 2-6,6-3,6-3 |
| ATP Delray Beach | 2021/01/07 19:30 | Gianluca Mager v Ryan Harrison | 3-6,6-1,6-4 |
| ATP Acapulco | 2020/02/23 01:00 | Daniel Altmaier v Ryan Harrison | 6-2,6-3 |
| ATP Delray Beach | 2020/02/19 17:30 | Soonwoo Kwon v Ryan Harrison | 6-4,3-6,7-6 |
| ATP Delray Beach | 2020/02/17 17:45 | Ryan Harrison v Damir Dzumhur | 6-3,6-2 |
| ITF M15 Monastir | 2021/01/12 09:00 | Tom Jomby v Kento Takeuchi | 6-2,5-7,1-6 |
| ITF M15 Monastir | 2021/01/06 08:00 | Tom Jomby v Luigi Castelletti | 4-6,6-4,4-6 |
| Eastern European Championship | 2020/11/26 12:30 | Tom Jomby v Nini Gabriel Dica | 6-4,6-2 |
| Eastern European Championship | 2020/11/24 17:10 | Tom Jomby v Mats Hermans | 6-1,6-0 |
| Eastern European Championship | 2020/11/23 11:10 | Tom Jomby v Tuna Altuna | 6-0,6-4 |
| Eastern European Championship | 2020/11/20 09:40 | Tom Jomby v Tomislav Brkic | 0-6,3-6 |
| Eastern European Championship | 2020/11/18 10:05 | Tom Jomby v Dragos Nicolae Madaras | 3-6,0-6 |
| Eastern European Championship | 2020/11/17 09:30 | Tom Jomby v Aziz Kijametovic | 1-6,4-6 |