| ITF USA F8 Qual | 03/18 18:00 | 62 | Philip Bester v Alafia Ayeni | 5-7,4-6 | |
| ITF USA F8 Qual | 03/17 17:00 | 62 | Philip Bester v Ryan Goetz | 7-5,6-3 | |
| Challenger Vancouver | 08/16 01:30 | 25 | [100] Ruben Bemelmans v Philip Bester [280] | 7-6,6-4 | |
| ATP Montreal Qual | 08/05 15:00 | 45 | [240] Philip Bester v James McGee [221] | 6-7,3-6 | |
| ATP Los Cabos Qual | 07/30 00:20 | 45 | [456] Philip Bester v Evan King [350] | 4-6,4-6 | |
| Challenger Granby | 07/25 22:30 | 25 | [169] Yasutaka Uchiyama v Philip Bester [456] | 6-4,6-4 | |
| Challenger Gatineau | 07/18 22:50 | 25 | [161] Denis Shapovalov v Philip Bester [456] | 6-3,3-6,6-3 | |
| Challenger Winnipeg | 07/11 23:00 | 25 | [245] Blaz Rola v Philip Bester [351] | 7-6,7-6 | |
| ITF Canada F3 | 06/29 21:00 | 26 | Philip Bester v Deiton Baughman | 6-7,4-6 | |
| ITF Canada F3 | 06/29 02:00 | 25 | Philip Bester v Mark Verryth | 6-3,7-6 | |
| ITF USA F19 | 06/22 15:40 | 26 | [400] Tommy Paul v Philip Bester [347] | 6-2,6-2 | |
| ITF USA F19 | 06/21 14:00 | 25 | Borna Gojo v Philip Bester | 6-3,0-6,5-7 | |
| ITF USA F16 | 05/03 14:00 | 25 | Philip Bester v Axel Geller | 1-6,6-1,0-6 | |
| ITF USA F13 | 04/16 18:00 | 29 | [362] Brayden Schnur v Philip Bester [383] | 7-6,6-1 | |
| ITF USA F13 | 04/15 16:00 | 28 | [500] Jared Hiltzik v Philip Bester [383] | 7-6,6-7,2-6 | |
| ITF USA F13 | 04/14 16:00 | 27 | [383] Philip Bester v Calvin Hemery [301] | 6-7,6-4,7-5 | |
| ITF USA F13 | 04/13 16:25 | 26 | Philip Bester v Ryan Shane | 6-3,6-3 | |
| ITF USA F13 | 04/12 15:00 | 25 | Philip Bester v Christopher G Haworth | 6-0,6-3 | |
| ITF USA F12 | 04/08 15:30 | 28 | [487] Takanyi Garanganga v Philip Bester [383] | 6-4,6-0 | |
| ITF USA F12 | 04/07 16:55 | 27 | Philip Bester v Jan Choinski | Walkover | |
| ITF USA F12 | 04/06 14:30 | 26 | Philip Bester v Gonzales Austin | 6-2,7-6 | |
| ITF USA F12 | 04/05 15:00 | 25 | Philip Bester v Yibing Wu | 5-7,6-2,6-4 | |
| Challenger Drummondville | 03/14 22:35 | 25 | [354] Philip Bester v John-Patrick Smith [243] | 3-6,4-6 | |
| ITF Canada F2 | 03/09 19:40 | 26 | [291] Gregoire Barrere v Philip Bester [354] | 6-4,6-2 | |
| ITF Canada F2 | 03/07 21:00 | 25 | Pavel Krainik v Philip Bester | 3-6,2-6 | |
| ITF Canada F1 | 03/01 16:15 | 25 | Philip Bester v JC Aragone | 5-7,6-2,5-7 | |
| ATP Delray Beach Qual | 02/18 20:50 | 26 | Philip Bester v Benjamin Becker | 2-6,7-6,2-6 | |
| Challenger Monterrey | 10/12 18:00 | 26 | Philip Bester v Marcelo Arevalo | Retired | |
| Challenger Monterrey | 10/10 18:00 | 25 | Philip Bester v Adam El Mihdawy | 6-4,6-4 | |
| Challenger Stockton Qual | 10/03 20:10 | 27 | Dennis Nevolo v Philip Bester | 6-1,4-6,6-3 |