Round: 25 Ground: Hardcourt outdoor
| Challenger Traralgon Qual | 2014/10/27 23:00 | Gavin Van Peperzeel v Darren Polkinghorne | 4-6,6-7 |
| ITF Australia F7 | 2014/10/08 02:30 | Christopher O'Connell v Gavin Van Peperzeel | 6-2,6-1 |
| ITF Turkey F27 | 2014/08/16 07:00 | Nikola Milojevic v Gavin Van Peperzeel | 7-5,7-5 |
| ITF Turkey F27 | 2014/08/15 07:00 | Ruan Roelofse v Gavin Van Peperzeel | 6-7,2-6 |
| ITF Turkey F27 | 2014/08/12 08:35 | Can Kaya v Gavin Van Peperzeel | 1-6,3-6 |
| ITF Serbia F8 | 2014/08/10 08:00 | Antonio Sancic v Gavin Van Peperzeel | 0-6,6-7 |
| ITF Serbia F8 | 2014/08/09 10:40 | Ilija Vucic v Gavin Van Peperzeel | 6-7,2-6 |
| ITF Serbia F8 | 2014/08/08 10:30 | Gavin Van Peperzeel v Miljan Zekic | 5-7,6-3,7-6 |
| Challenger Traralgon | 2014/10/28 02:25 | Kyle Edmund v Bradley Klahn | 6-7,1-6 |
| Challenger Tiburon | 2014/10/06 19:40 | Kyle Edmund v James McGee | 6-3,3-6,3-6 |
| Challenger Shanghai | 2014/09/03 05:35 | Tsung-Hua Yang v Kyle Edmund | 7-5,6-2 |
| Challenger Segovia | 2014/08/01 14:20 | Adrian Menendez-Maceiras v Kyle Edmund | 4-6,6-4,7-6 |
| Challenger Segovia | 2014/07/31 15:50 | Kyle Edmund v Roberto Ortega-Olmedo | 6-2,6-2 |
| Challenger Recanati | 2014/07/15 19:35 | Kyle Edmund v Marc Giner | 6-1,6-4 |
| Wimbledon | 2014/06/23 15:45 | Andreas Haider-Maurer v Kyle Edmund | 6-3,7-6,6-2 |
| ATP Miami | 2014/03/19 18:20 | Julien Benneteau v Kyle Edmund | 6-7,6-3,6-2 |