Janko Tipsarevic defeated Novak Djokovic 7-6 6-3 in the Madrid Masters quarter-final on clay. The upset overturned the form book — Novak Djokovic came in leading the head-to-head 6–1, defending last year's semi-final. Janko Tipsarevic narrowed the head-to-head to 6–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2012-08-06 | Canada Masters | SF | hard | Novak Djokovic | 6-4 6-1 |
| 2012-02-27 | Dubai | QF | hard | Novak Djokovic | 6-1 7-6 |
| 2011-11-20 | Tour Finals | RR | hard | Janko Tipsarevic | 3-6 6-3 6-3 |
| 2011-08-29 | US Open | QF | hard | Novak Djokovic | 7-6 6-7 6-0 3-0 |
| 2009-05-04 | Belgrade | R16 | hard | Novak Djokovic | 6-2 4-6 6-0 |
| 2008-06-12 | London | R16 | carpet | Novak Djokovic | 2-6 6-1 6-4 |
| 2008-06-09 | Queen's Club | R16 | grass | Novak Djokovic | 2-6 6-1 6-4 |
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.
Performance in the biggest moments — break points, deciding sets and tiebreaks (0–100, higher is better). About
Djokovic N.: 5 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