Stadium: LA FORET 4 Round: 45 Ground: Hardcourt outdoor
| Challenger Izmir Qual | 2016/09/17 09:00 | Roelofse, Ruan v O'Brien, Dean | 6-0,6-3 |
| Aptos, USA, Qualifications | 2016/08/07 17:00 | Cameron Norrie v O'Brien, Dean | 6-1,6-1 |
| Aptos, USA, Qualifications | 2016/08/06 20:10 | Genender, Michael v O'Brien, Dean | 3-6,2-6 |
| Challenger Dallas Qual | 2016/01/30 16:00 | O'Brien, Dean v Thompson, Clay | 4-6,2-6 |
| Challenger Columbus | 2015/09/21 18:55 | O'Brien, Dean v Bangoura, Sekou | 3-6,1-6 |
| Columbus, USA, Qualifications | 2015/09/20 16:10 | O'Brien, Dean v Pollanen, Herkko | 6-3,6-4 |
| ITF Uzbekistan F4 | 2015/06/10 06:25 | Ismailov, Temur v O'Brien, Dean | 6-2,6-1 |
| ITF Uzbekistan F4 | 2015/06/09 07:40 | O'Brien, Dean v Tsoy, Pavel | 6-3,6-4 |
| St. Petersburg, Russia, Qualifying | 2016/09/19 08:00 | Daniil Medvedev v Pavic, Ante | 6-4,6-2 |
| St. Petersburg, Russia, Qualifying | 2016/09/18 08:00 | Pavic, Ante v Ward, James | 7-6,6-2 |
| Istanbul, Turkey | 2016/09/15 10:00 | Pavic, Ante v Chiudinelli, Marco | 1-6,2-6 |
| Istanbul, Turkey | 2016/09/13 11:00 | Pavic, Ante v Matsukevitch, Denis | 6-1,6-2 |
| Challenger St Remy | 2016/09/06 09:00 | Pavic, Ante v Yannick Hanfmann | 3-6,3-6 |
| Manerbio, Italie, Qualifications | 2016/08/20 15:30 | Pavic, Ante v Eysseric, Jonathan | 4-6,4-6 |
| Challenger Astana 2 | 2016/07/28 07:25 | Duckhee Lee v Pavic, Ante | 6-1,6-2 |
| Challenger Astana 2 | 2016/07/26 05:00 | Kedriouk, Alexey v Pavic, Ante | 1-6,0-6 |