Round: 29 Ground: Hardcourt outdoor
| ITF Sweden F4 | 2016/09/29 09:15 | Christopher O'Connell v Sam Barry | 4-6,6-3,6-7 |
| ITF Sweden F4 | 2016/09/28 08:00 | Christopher O'Connell v Milos Sekulic | 4-6,7-6,6-0 |
| ITF Sweden F4 | 2016/09/27 09:00 | Christopher O'Connell v Daniel Svensson | 6-1,6-4 |
| Challenger Sibiu | 2016/09/24 11:20 | Lorenzo Giustino v Christopher O'Connell | 6-7,6-4,7-5 |
| Challenger Sibiu | 2016/09/23 11:05 | Vaclav Safranek v Christopher O'Connell | 7-6,1-6,1-6 |
| Challenger Sibiu | 2016/09/21 10:00 | Tristan Lamasine v Christopher O'Connell | 1-6,2-6 |
| Challenger Sibiu | 2016/09/20 12:30 | Christopher O'Connell v Gerald Melzer | 6-4,6-4 |
| Challenger Sibiu Qual | 2016/09/19 10:30 | Christopher O'Connell v Filipp Kekercheni | 6-3,6-4 |
| ITF Australia F7 | 2016/10/06 01:55 | Adam Walton v Max Purcell | 4-6,4-6 |
| ITF Australia F7 | 2016/10/04 02:05 | Nathan Pasha v Max Purcell | 4-6,6-3,3-6 |
| ITF Australia F6 | 2016/10/01 03:00 | Max Purcell v Jarmere Jenkins | 2-6,2-6 |
| ITF Australia F6 | 2016/09/30 02:05 | Luke Saville v Max Purcell | 2-6,1-6 |
| ITF Australia F6 | 2016/09/29 00:00 | Darren Polkinghorne v Max Purcell | 2-6,6-2,1-6 |
| ITF Australia F6 | 2016/09/27 02:45 | Jeremy Beale v Max Purcell | 6-7,6-4,0-6 |
| ITF Australia F5 | 2016/09/20 02:15 | Bradley Mousley v Max Purcell | 4-6,6-1,7-6 |
| ITF Australia F2 | 2016/03/02 23:00 | Max Purcell v Bradley Mousley | 4-6,3-6 |