| 28‑Jun‑2021 | Wimbledon | Grass | QF | 8 | 18 | (14)Hubert Hurkacz [POL] d. (6)Federer | 6-3 7-6(4) 6-0 | (ch) | 0.68 | 5.4% | 3.2% | 64.5% | 66.7% | 33.3% | 10/15 | 1:49 |
| 25‑May‑2008 | Roland Garros | Clay | F | 1 | 2 | (2)Rafael Nadal [ESP] d. (1)Federer | 6-1 6-3 6-0 | (ch) | 0.52 | 2.6% | 0.0% | 68.8% | 49.1% | 20.8% | 9/17 | 1:48 |
| 7‑Jun‑1999 | Queen's Club | Grass | R64 | 104 | 37 | (13)Byron Black [ZIM] d. Federer | 6-3 6-0 | | 0.60 | 0.0% | 7.3% | 60.0% | 45.5% | 40.9% | 3/8 | 0:52 |
| 24‑May‑1999 | Roland Garros | Clay | R128 | 111 | 3 | (3)Patrick Rafter [AUS] d. (WC)Federer | 5-7 6-3 6-0 6-2 | | 0.75 | 2.8% | 2.8% | 55.6% | 61.7% | 50.0% | 10/17 | 2:13 |
| 19‑Apr‑1999 | Monte Carlo Masters | Clay | R64 | 128 | 33 | Vincent Spadea [USA] d. (WC)Federer | 7-6(3) 6-0 | | 0.47 | 0.0% | 3.2% | 53.2% | 60.6% | 51.7% | 4/7 | 1:05 |
| 23‑Aug‑1997 | Switzerland 1 Masters 2 | Clay | R16 | | 228 | (1)Agustin Garizzio [ARG] d. Federer | 4-6 6-0 6-4 | | | | | | | | | |
| 23‑Aug‑1997 | Switzerland 1 Masters 4 | Clay | R16 | | | (5)Federer d. (WC)Joel Spicher [SUI] | 6-3 0-6 6-4 | | | | | | | | | |
