Round: 25 Ground: Hardcourt outdoor
| Challenger Canberra 2 Qual | 2016/10/30 00:10 | Greg Jones v Nathan Pasha | 3-6,6-4,7-6 |
| Challenger Canberra 2 Qual | 2016/10/29 01:55 | Greg Jones v Dimitri Morogiannis | 6-0,6-4 |
| Challenger Traralgon | 2016/10/25 23:00 | Matt Reid v Greg Jones | 6-4,6-4 |
| Challenger Las Vegas Qual | 2016/10/17 17:30 | Lloyd Glasspool v Greg Jones | 6-4,7-6 |
| Challenger Las Vegas Qual | 2016/10/16 21:00 | Greg Jones v Erik Crepaldi | 6-0,6-7,7-5 |
| Challenger Las Vegas Qual | 2016/10/15 20:55 | Greg Jones v Alexios Halebian | 2-6,7-6,6-3 |
| Challenger Fairfield Qual | 2016/10/09 19:05 | Hans Podlipnik-Castillo v Greg Jones | 6-4,3-6,6-3 |
| Challenger Fairfield Qual | 2016/10/08 21:30 | Connor Farren v Greg Jones | 6-7,3-6 |
| Challenger Canberra 2 Qual | 2016/10/29 23:00 | Daniel Masur v Darren Polkinghorne | 6-1,1-6,7-6 |
| Challenger Canberra 2 Qual | 2016/10/28 23:30 | Arjun Mehrotra v Darren Polkinghorne | 1-6,2-6 |
| Challenger Traralgon | 2016/10/25 00:35 | Darren Polkinghorne v Matthew Barton | 6-7,4-6 |
| ITF Australia F8 | 2016/10/12 00:00 | Blake Mott v Darren Polkinghorne | 6-2,6-1 |
| ITF Australia F7 | 2016/10/06 00:00 | Darren Polkinghorne v Marc Polmans | 4-6,4-6 |
| ITF Australia F7 | 2016/10/04 02:10 | Kody Pearson v Darren Polkinghorne | 3-6,4-6 |
| 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 00:00 | Lucas Vuradin v Darren Polkinghorne | 4-6,3-6 |