Stadium: Court 5 Round: 14 Ground: Hardcourt indoor
| ITF M15 Naples | 2021/10/10 14:00 | Antoine Cornut-Chauvinc v Ryan Harrison | 3-6,5-7 |
| ITF M15 Naples | 2021/10/09 14:00 | Damien Wenger v Ryan Harrison | 3-6,5-7 |
| ITF M15 Naples | 2021/10/08 14:30 | Peter Bertran v Ryan Harrison | 3-6,1-6 |
| ITF M15 Naples | 2021/10/07 15:35 | Juncheng Shang v Ryan Harrison | 3-6,2-6 |
| ITF M15 Naples | 2021/10/06 19:25 | Louroi Martinez v Ryan Harrison | 6-7,3-6 |
| Challenger Barletta | 2021/08/23 11:00 | Luca Potenza v Ryan Harrison | 3-6,6-3,2-6 |
| Challenger Barletta | 2021/08/22 12:50 | Ryan Harrison v Alexis Galarneau | 6-4,6-3 |
| ITF M25 Ueberlingen | 2021/08/20 11:30 | Ryan Harrison v Eduard Esteve Lobato | 1-6,4-6 |
| ATP Sydney | 2022/01/09 00:00 | Daniel Altmaier v Michail Pervolarakis | 6-4,6-1 |
| ATP Cup | 2022/01/05 06:30 | Michail Pervolarakis v Aleksandre Metreveli | 6-3,6-2 |
| ATP Cup | 2022/01/03 06:30 | Michail Pervolarakis v Federico Delbonis | 6-7,1-6 |
| ATP Cup | 2022/01/01 06:30 | Michail Pervolarakis v Kamil Majchrzak | 1-6,4-6 |
| Challenger Forli | 2021/12/10 15:30 | Andrea Arnaboldi v Michail Pervolarakis | 6-4,6-3 |
| Challenger Forli | 2021/12/09 17:35 | Michail Pervolarakis v Filippo Baldi | 6-4,6-4 |
| Challenger Forli | 2021/12/07 11:40 | Michail Pervolarakis v Luca Potenza | 6-3,6-4 |
| Challenger Manama | 2021/11/22 09:55 | Vladyslav Orlov v Michail Pervolarakis | 1-6,6-4,6-0 |