| Challenger - Barcelona | 10/08 13:00 | 26 | Carlos Gimeno Valero v Christopher O'Connell | Retired | |
| Challenger - Barcelona | 10/06 08:00 | 25 | [151] Alex Bolt v Christopher O'Connell [112] | 1-6,2-6 | |
| Challenger - Biella | 10/03 15:00 | 28 | [129] Facundo Bagnis v Christopher O'Connell [112] | 6-4,6-4 | |
| Challenger - Biella | 10/03 10:30 | 27 | [169] Denis Istomin v Christopher O'Connell [112] | 3-6,3-6 | |
| Challenger - Biella | 10/01 12:35 | 26 | [206] Juan Pablo Ficovich v Christopher O'Connell [112] | 7-5,4-6,1-6 | |
| Challenger - Biella | 09/29 08:00 | 25 | [199] Ramkumar Ramanathan v Christopher O'Connell [112] | 4-6,2-6 | |
| Open de França | 09/21 12:55 | 14 | [111] Christopher O'Connell v Elias Ymer [185] | 5-7,4-6 | |
| Challenger - Aix en Provence | 09/08 09:45 | 25 | Christopher O'Connell v Oscar Otte | Cancelled | |
| Open dos EUA | 09/03 22:15 | 24 | [116] Christopher O'Connell v Daniil Medvedev [5] | 3-6,2-6,4-6 | |
| Open dos EUA | 09/01 22:25 | 23 | [116] Christopher O'Connell v Laslo Djere [81] | 4-6,6-4,7-6,6-4 | |
| Sydney - UTR Pro Tennis Series | 07/09 01:00 | - | Christopher O'Connell v Rinky Hijikata | 3-6,0-0 | |
| Sydney - UTR Pro Tennis Series | 07/08 04:00 | - | Christopher O'Connell v James McCabe | 6-3,6-1 |