| Stockton, USA, Qualifying | 10/02 17:50 | 26 | Santiago, Mico v Bester, Philip | 3-6,1-6 | |
| Stockton, USA, Qualifying | 10/01 20:55 | 25 | Bester, Philip v Langer, Nils | 6-3,7-6 | |
| Challenger Columbus | 09/20 16:50 | 25 | 산드그렌, 테니스 v Bester, Philip | 6-4,6-4 | |
| Challenger Cary | 09/15 18:45 | 26 | Bester, Philip v 코즐로브, 스테판 | 4-6,1-6 | |
| Challenger Cary | 09/13 16:00 | 25 | Bester, Philip v Meister, Nicolas | 7-5,6-3 | |
| Canada F7, Singles | 09/08 16:00 | 26 | 볼프슨, 다비드 v Bester, Philip | 7-6,1-6,6-3 | |
| Canada F7, Singles | 09/06 17:35 | 25 | Carter, Andrew v Bester, Philip | 3-6,2-6 | |
| ITF Canada F6 | 09/03 18:00 | 28 | Bester, Philip v 슈너, 브라이덴 | 4-6,6-3,3-6 | |
| ITF Canada F6 | 09/02 18:15 | 27 | Bester, Philip v Austin, Gonzales | 7-5,6-3 | |
| ITF Canada F6 | 09/01 18:55 | 26 | Bester, Philip v Frljanic, Stefan | 4-6,7-6,7-5 | |
| ITF Canada F6 | 08/30 16:00 | 25 | Bester, Philip v Scott, Harrison | 7-5,6-2 | |
| Challenger Granby | 08/04 22:30 | 26 | 우치야마, 야스타카 v Bester, Philip | 6-4,7-5 | |
| Challenger Granby | 08/02 16:05 | 25 | Bester, Philip v 할리스, 퀸틴 | 6-2,7-6 | |
| Challenger Winnipeg | 07/15 15:00 | 27 | Bester, Philip v 고조우지크, 피터 | 5-7,3-6 | |
| Challenger Winnipeg | 07/14 15:20 | 26 | 프라탄젤로, 비오른 v Bester, Philip | 6-4,5-7,1-6 | |
| Challenger Winnipeg | 07/12 20:35 | 25 | 슈너, 브라이덴 v Bester, Philip | 1-6,3-6 | |
| ITF Canada F5 | 07/10 17:00 | 29 | Bester, Philip v 폴란스키, 페터 | 6-4,4-6,6-4 | |
| ITF Canada F5 | 07/09 17:00 | 28 | Bester, Philip v 모트, 블랙 | 6-4,4-6,6-4 | |
| ITF Canada F5 | 07/08 19:10 | 27 | Bester, Philip v 슈너, 브라이덴 | 6-3,6-2 | |
| ITF Canada F5 | 07/07 18:35 | 26 | Bester, Philip v 갈라르네아우, 알렉시스 | 6-4,7-5 | |
| ITF Canada F5 | 07/06 21:00 | 25 | Bester, Philip v Krustev, Victor | 6-4,6-1 | |
| ITF Canada F4 | 07/01 19:25 | 27 | Bester, Philip v 볼트즈, 세바스티엔 | 6-7,4-6 | |
| ITF Canada F4 | 06/30 17:00 | 26 | Bester, Philip v 페크, 조수아 | 6-3,6-2 | |
| ITF Canada F4 | 06/29 18:35 | 25 | Bester, Philip v Kylar, Kevin | 6-1,6-3 | |
| ITF Canada F3 | 06/24 18:00 | 27 | 폴란스키, 페터 v Bester, Philip | 4-6,6-3,6-2 | |
| ITF Canada F3 | 06/23 17:00 | 26 | Genender, Michael v Bester, Philip | 1-6,0-6 | |
| ITF Canada F3 | 06/22 18:35 | 25 | Kylar, Kevin v Bester, Philip | 2-6,1-6 | |
| ITF USA F17 | 06/08 15:50 | 25 | Bester, Philip v Cotrone, Dominic | 6-3,3-6,6-3 | |
| ITF USA F16 | 05/07 14:00 | 28 | 쿠이로즈, 로베르토 v Bester, Philip | 6-2,6-4 | |
| ITF USA F16 | 05/06 14:00 | 27 | Bester, Philip v 케크마노비치, 미오밀 | 7-5,6-3 |