Christopher O'Connell 6-7,6-7 Dimitar Grabul 2016-07-01 14:30
Round: 27 Ground: Clay
Home History
| ITF Macedonia F2 | 2016/06/30 08:00 | Christopher O'Connell v Ljubomir Celebic | 6-2,7-5 |
| ITF Macedonia F2 | 2016/06/28 07:30 | Christopher O'Connell v Besir Durguti | 7-5,6-2 |
| ITF Macedonia F1 | 2016/06/24 10:20 | Lenny Hampel v Christopher O'Connell | 7-6,6-2 |
| ITF Macedonia F1 | 2016/06/23 14:00 | Kristijan Mesaros v Christopher O'Connell | 7-5,5-7,0-6 |
| ITF Macedonia F1 | 2016/06/21 07:30 | Ljubomir Celebic v Christopher O'Connell | 4-6,1-6 |
| ITF Italy F14 | 2016/06/10 08:00 | Christopher O'Connell v Maverick Banes | 4-6,0-6 |
| ITF Italy F14 | 2016/06/08 11:35 | Christopher O'Connell v Kenneth Raisma | 2-6,7-6,6-3 |
| ITF Italy F14 | 2016/06/06 17:30 | Christopher O'Connell v Filippo Mora | 6-0,6-1 |
Away History
| ITF Macedonia F2 | 2016/06/30 13:30 | Dimitar Grabul v Lenny Hampel | 6-0,4-6,6-1 |
| ITF Macedonia F2 | 2016/06/29 13:05 | Dimitar Grabul v Duje Kekez | 6-3,7-6 |
| Davis Cup | 2016/03/05 15:20 | Dimitar Grabul v Rrezart Cungu | 6-2,6-0 |
| Davis Cup | 2016/03/02 14:00 | Dimitar Grabul v Mikayel Khachatryan | 6-4,6-0 |
| ITF Switzerland F1 | 2016/02/10 11:15 | Dimitar Grabul v Yann Marti | 5-7,0-6 |
| ITF Switzerland F1 | 2016/02/09 14:15 | Pablo Vivero Gonzalez v Dimitar Grabul | 6-4,3-6,4-6 |
| ITF Switzerland F1 Qual | 2016/02/07 10:00 | Dominik Boehler v Dimitar Grabul | 6-4,2-6,4-6 |
| Davis Cup | 2015/07/17 09:00 | Dimitar Grabul v Casper Ruud | 6-1,1-6,2-6 |