Round: 29 Ground: Hardcourt outdoor
| Challenger Canberra 2 | 2016/10/31 02:00 | Christopher O'Connell v Omar Jasika | 4-6,4-6 |
| Challenger Traralgon | 2016/10/24 23:00 | Christopher O'Connell v Grega Zemlja | 2-6,6-3,4-6 |
| ITF Australia F8 | 2016/10/16 05:00 | Christopher O'Connell v Blake Mott | 0-6,6-2,6-4 |
| ITF Australia F8 | 2016/10/16 01:00 | Dayne Kelly v Christopher O'Connell | 3-6,6-2,4-6 |
| ITF Australia F8 | 2016/10/14 01:00 | Christopher O'Connell v Maverick Banes | 6-2,7-6 |
| ITF Australia F8 | 2016/10/13 01:00 | Christopher O'Connell v Thomas Fancutt | 6-3,6-2 |
| ITF Australia F8 | 2016/10/11 00:00 | Christopher O'Connell v Dimitri Vidin | 6-0,6-1 |
| ITF Sweden F4 | 2016/09/29 09:15 | Christopher O'Connell v Sam Barry | 4-6,6-3,6-7 |
| ITF Australia F9 | 2016/11/09 23:00 | Max Purcell v Harry Bourchier | 5-7,7-5,1-6 |
| ITF Australia F9 | 2016/11/07 23:00 | Max Purcell v Scott Puodziunas | 7-5,7-6 |
| Challenger Canberra 2 | 2016/11/02 00:00 | Max Purcell v Greg Jones | 3-6,6-7 |
| Challenger Canberra 2 | 2016/10/31 23:30 | Max Purcell v Harry Bourchier | 6-4,7-6 |
| ITF Australia F7 | 2016/10/08 02:30 | Jarmere Jenkins v Max Purcell | 6-7,6-4,6-4 |
| ITF Australia F7 | 2016/10/07 00:00 | Dayne Kelly v Max Purcell | 6-7,2-6 |
| 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 |