
Gael Monfils defeated Novak Djokovic 6-4 6-7 6-2 in the Italy F4 qualifying round on clay. The upset overturned the form book — Novak Djokovic came in ranked #5, leading the head-to-head 19–0. Gael Monfils claimed a first win over Novak Djokovic in 20 meetings, narrowing the head-to-head to 19–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-12-30 | Brisbane | R16 | hard | Novak Djokovic | 6-3 6-3 |
| 2023-08-14 | Cincinnati Masters | R16 | hard | Novak Djokovic | 6-3 6-2 |
| 2022-05-02 | Madrid Masters | R32 | clay | Novak Djokovic | 6-3 6-2 |
| 2020-02-24 | Dubai | SF | hard | Novak Djokovic | 2-6 7-6 6-1 |
| 2020-01-06 | Atp Cup | RR | hard | Novak Djokovic | 6-3 6-2 |
| 2018-01-15 | Australian Open | R64 | hard | Novak Djokovic | 4-6 6-3 6-1 6-3 |
| 2017-06-26 | Eastbourne | F | grass | Novak Djokovic | 6-3 6-4 |
| 2016-08-29 | US Open | SF | hard | Novak Djokovic | 6-3 6-2 3-6 6-2 |
| 2016-07-25 | Canada Masters | SF | hard | Novak Djokovic | 6-3 6-2 |
| 2014-10-27 | Paris Masters | R16 | hard | Novak Djokovic | 6-3 7-6 |
| 2014-08-04 | Canada Masters | R32 | hard | Novak Djokovic | 6-2 6-7 7-6 |
| 2013-10-07 | Shanghai Masters | QF | hard | Novak Djokovic | 6-7 6-2 6-4 |
| 2011-08-14 | Cincinnati Masters | QF | hard | Novak Djokovic | 3-6 6-4 6-3 |
| 2010-12-03 | Davis Cup WG F: SRB vs FRA | RR | hard | Novak Djokovic | 6-2 6-2 6-4 |
| 2010-08-30 | US Open | QF | hard | Novak Djokovic | 7-6 6-1 6-2 |
| 2009-11-08 | Paris Masters | F | hard | Novak Djokovic | 6-2 5-7 7-6 |
| 2008-08-11 | Beijing Olympics | QF | hard | Novak Djokovic | 4-6 6-1 6-4 |
| 2006-05-29 | Roland Garros | R16 | clay | Novak Djokovic | 7-6 7-6 6-3 |
| 2005-08-29 | US Open | R128 | hard | Novak Djokovic | 7-5 4-6 7-6 0-6 7-5 |
Averages over each player's completed matches in the selected window (199 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Monfils G.: 6 days rest · 1 match, 30 games (7d) · Djokovic N.: 4 days rest · 1 match, 28 games (7d). Higher means fresher. About
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About