Stadium: Center Court Round: 27 Ground: Clay
| Australian Open 2017 | 2017/01/17 08:00 | Grigor Dimitrov v Christopher O'Connell | 7-6,6-3,6-3 |
| Challenger Kobe | 2022/11/19 03:35 | Christopher O'Connell v Yosuke Watanuki | 4-6,6-7 |
| Challenger Kobe | 2022/11/18 02:00 | Christopher O'Connell v Marc Polmans | 7-5,7-6 |
| Challenger Kobe | 2022/11/17 03:40 | Christopher O'Connell v Beibit Zhukayev | 6-2,6-7,6-1 |
| Challenger Kobe | 2022/11/15 05:05 | Christopher O'Connell v Colin Sinclair | 6-7,7-6,7-6 |
| Challenger Yokohama | 2022/11/06 02:00 | Christopher O'Connell v Yosuke Watanuki | 6-1,6-7,6-3 |
| Challenger Yokohama | 2022/11/05 02:00 | Christopher O'Connell v Sho Shimabukuro | 6-3,6-3 |
| Challenger Yokohama | 2022/11/04 02:00 | Christopher O'Connell v Tung-Lin Wu | 6-7,7-6,6-4 |
| Challenger Yokohama | 2022/11/02 01:30 | Christopher O'Connell v Ergi Kirkin | 6-3,6-4 |
| United Cup | 2022/12/31 04:00 | David Goffin v Grigor Dimitrov | 4-6,5-7 |
| United Cup | 2022/12/29 06:35 | Stefanos Tsitsipas v Grigor Dimitrov | 4-6,6-2,7-6 |
| World Tennis League | 2022/12/21 17:10 | Grigor Dimitrov v Nick Kyrgios | 7-6,6-3 |
| ATP Paris | 2022/11/03 12:40 | Carlos Alcaraz Garfia v Grigor Dimitrov | 6-1,6-3 |
| ATP Paris | 2022/11/02 15:40 | Grigor Dimitrov v Fabio Fognini | 6-0,7-5 |
| ATP Paris | 2022/11/01 15:50 | Botic Van De Zandschulp v Grigor Dimitrov | 6-7,6-7 |
| ATP Vienna | 2022/10/29 12:00 | Daniil Medvedev v Grigor Dimitrov | 6-4,6-2 |
| ATP Vienna | 2022/10/28 12:00 | Grigor Dimitrov v Marcos Giron | 6-3,4-6,6-4 |