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Novak Djokovic currently trails world number one Jannik Sinner by two sets in the duo’s meeting in the semifinals of the 2025 Wimbledon men’s singles.
Djokovic must now come from two sets behind in order to progress to the next round. This is a feat the Serb has achieved eight times previously in Grand Slams.
The most recent of these came in 2023, when Djokovic came from two sets behind to defeat compatriot Laslo Djere in the third round of the US Open to win 4-6, 4-6, 6-1, 6-1, 6-3. Djokovic has also defeated Sinner at Wimbledon by coming from two sets down before, winning their 2022 Wimbledon quarterfinal 5-7, 2-6, 6-3, 6-2, 6-2.
Djokovic also won the 2021 Roland Garros by coming back from two sets behind to defeat Greece’s Stefanos Tsitsipas 6-7(6), 2-6, 6-3, 6-2, 6-4.
Here is a list of all the times Djokovic has come from two sets behind to win in a Grand Slam:
| Year | Major | Opponent | Round | Score |
| 2005 | Wimbledon | Guillermo Garcia-Lopez (Spain) | Second | 3-6, 3-6, 7-6(5), 7-6(3), 6-4 |
| 2011 | US Open | Roger Federer (Switzerland) | Semifinal | 6-7(7), 4-6, 6-3, 6-2, 7-5 |
| 2012 | Roland Garros | Andreas Seppi (Italy) | Fourth | 4-6, 6-7(5), 6-3, 7-5, 6-3 |
| 2015 | Wimbledon | Kevin Anderson (South Africa) | Fourth | 6-7(6), 6-7(6), 6-1, 6-4, 7-5 |
| 2021 | Roland Garros | Lorenzo Musetti (Italy) | Fourth | 6-7(7), 6-7(2), 6-1, 6-0, 4-0, retd. |
| 2021 | Roland Garros | Stefanos Tsitsipas (Greece) | Final | 6-7(6), 2-6, 6-3, 6-2, 6-4 |
| 2022 | Wimbledon | Jannik Sinner (Italy) | Quarterfinal | 5-7, 2-6, 6-3, 6-2, 6-2 |
| 2023 | US Open | Laslo Djere (Serbia) | Third | 4-6, 4-6, 6-1, 6-1, 6-3 |
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