| 2016-03-04 | Davis Cup WG R1: CAN vs FRA | Clay | RR | 10 |  Richard Gasquet | 274 |  Philip Bester | 6-1 7-6(4) | H2H | 3 | 81 | 6 | 2 | 55.4% | 83.9% | 76.0% | 0/0 |
| 2015-08-10 | Canada Masters | Hard | R64 | 46 |  Gilles Muller | 225 | Philip Bester (WC) | 6-2 6-3 | H2H | 3 | 69 | 13 | 2 | 44.6% | 84.0% | 61.3% | 2/2 |
| 2011-07-08 | Davis Cup G1 R2: ECU vs CAN | Clay | RR | 384 |  Julio Cesar Campozano | 229 | Philip Bester | 7-6(4) 6-7(4) 7-5 6-2 | H2H | 5 | - | - | - | - | - | - | - |
| 2011-07-08 | Davis Cup G1 R2: ECU vs CAN | Clay | RR | 229 | Philip Bester | 497 | Ivan Endara | 6-2 7-6(3) 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 2010-08-22 | New Haven | Hard | R32 | 79 |  Illya Marchenko | 383 | Philip Bester (Q) | 6-3 6-3 | H2H | 3 | 81 | 3 | 1 | 61.5% | 81.3% | 50.0% | 2/3 |
| 2007-08-05 | Canada Masters | Hard | R64 | 47 | Arnaud Clement | 660 | Philip Bester (WC) | 7-6(2) 6-2 | H2H | 3 | 77 | 5 | 1 | 70.2% | 75.0% | 82.4% | 2/3 |
| 2006-08-07 | Canada Masters | Hard | R64 | 6 |  James Blake (5) | 705 | Philip Bester (WC) | 6-4 6-1 | H2H | 3 | 56 | 4 | 2 | 53.7% | 81.8% | 73.7% | 0/0 |
| 2006-07-21 | Davis Cup G1 PO: CAN vs VEN | Hard | RR | 700 | Philip Bester | - |  Jhonathan Medina-Alvarez | 7-5 6-4 2-6 6-4 | H2H | 5 | - | - | - | - | - | - | - |
| 2006-04-07 | Davis Cup G1 R2: MEX vs CAN | Clay | RR | 351 |  Bruno Echagaray | 765 | Philip Bester | 6-3 7-6(4) | H2H | 3 | - | - | - | - | - | - | - |
| 2005-08-08 | Canada Masters | Hard | R64 | 56 |  Ricardo Mello | 978 | Philip Bester (WC) | 6-4 6-2 | H2H | 3 | 62 | 4 | 2 | 63.8% | 83.8% | 57.1% | 2/2 |
