stylistic:tone
Roger Federer

Djokovic and Roger Federer's rivalry is considered to be one of the greatest rivalries in tennis history. They faced each other 50 times, with Djokovic leading 27–23, including 13–6 in finals (not including a 2014 walkover in favor of Djokovic). Djokovic leads on hard courts 20–18 as well as on grass 3–1 and they are split 4–4 on clay.

Djokovic is the player with the most victories over Federer and the only player to beat Federer multiple times at his most successful major tournaments, four times at the Australian Open, three times at the US Open, three times at the Year-end Championship and most notably, three times at the final of Wimbledon Championships. Their most recent final was at the 2019 Wimbledon where Djokovic won in five sets in what became the longest final in Wimbledon history. Other notable matches they contested are the 2014 Wimbledon and 2015 Wimbledon finals, along with semifinals at the 2010 US Open, 2011 US Open, 2011 French Open, and 2018 Paris Masters.