Stadium: Court 1 Round: 64 Ground: Hardcourt outdoor
| Challenger Barcelona | 2020/10/06 08:00 | Alex Bolt v Christopher O'Connell | 1-6,2-6 |
| Challenger Biella | 2020/10/03 15:00 | Facundo Bagnis v Christopher O'Connell | 6-4,6-4 |
| Challenger Biella | 2020/10/03 10:30 | Denis Istomin v Christopher O'Connell | 3-6,3-6 |
| Challenger Biella | 2020/10/01 12:35 | Juan Pablo Ficovich v Christopher O'Connell | 7-5,4-6,1-6 |
| Challenger Biella | 2020/09/29 08:00 | Ramkumar Ramanathan v Christopher O'Connell | 4-6,2-6 |
| French Open | 2020/09/21 12:55 | Christopher O'Connell v Elias Ymer | 5-7,4-6 |
| US Open | 2020/09/03 22:15 | Christopher O'Connell v Daniil Medvedev | 3-6,2-6,4-6 |
| US Open | 2020/09/01 22:25 | Christopher O'Connell v Laslo Djere | 4-6,6-4,7-6,6-4 |
| Australian Open | 2021/01/10 11:45 | Cedrik-Marcel Stebe v Thomas Fabbiano | 6-1,4-6,7-6 |
| Italian National Tour | 2020/07/01 09:45 | Matteo Gigante v Thomas Fabbiano | 6-3,2-6,6-3 |
| Italian National Tour | 2020/06/30 08:25 | Luciano Darderi v Thomas Fabbiano | 4-6,2-6 |
| Italian Umbrian Open | 2020/06/25 10:30 | Andrea Vavassori v Thomas Fabbiano | 7-6,6-4 |
| Italian Umbrian Open | 2020/06/25 08:00 | Andrea Vavassori v Thomas Fabbiano | 2-2 |
| Italian Umbrian Open | 2020/06/23 12:45 | Matteo Gigante v Thomas Fabbiano | 4-6,6-4,7-10 |
| ATP Dubai | 2020/02/22 08:45 | Lloyd Harris v Thomas Fabbiano | 5-7,6-4,6-3 |
| Challenger Bengaluru | 2020/02/14 09:55 | James Duckworth v Thomas Fabbiano | 6-7,6-0,6-2 |