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