Jiri Novak defeated Roger Federer 6-1 2-6 7-5 in the Monte Carlo Masters round of 64 on clay. The upset overturned the form book — Roger Federer came in leading the head-to-head 5–3, defending last year's round of 64. Jiri Novak narrowed the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-06-07 | Halle | SF | grass | Roger Federer | 6-3 6-4 |
| 2003-07-07 | Gstaad | F | clay | Jiri Novak | 5-7 6-3 6-3 1-6 6-3 |
| 2003-02-24 | Dubai | F | hard | Roger Federer | 6-1 7-6(2) |
| 2002-11-11 | Masters Cup | RR | hard | Roger Federer | 6-0 4-6 6-2 |
| 2002-10-07 | Vienna | F | hard | Roger Federer | 6-4 6-1 3-6 6-4 |
| 2001-10-29 | Paris Masters | R32 | hard | Jiri Novak | 6-4 6-7(4) 7-6(2) |
| 1999-10-11 | Vienna | R16 | hard | Roger Federer | 7-6(8) 6-1 |
| 1999-06-21 | Wimbledon | R128 | grass | Jiri Novak | 6-3 3-6 4-6 6-3 6-4 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.