The 38-year-old reached a century of wins at the French Open last month and is now a two-time member of the exclusive 100 club.
Djokovic is also one shy of 100 wins at the Australian Open, where he is a 10-time winner, and providing he plays there in 2026, he could put himself on the brink of becoming the first player to win 100 matches at three different slams.
"In all his years at Wimbledon, he won't have played many finer rallies than that!" Brilliant entertainment on Centre Court #Wimbledon pic.twitter.com/FFnSXR3Y1F
— BBC Sport (@BBCSport) July 5, 2025Chris Evert, Martina Navratilova and Serena Williams all reached the milestone at one major apiece, and here we rank their efforts based on their conversion from matches played to titles won.
The Serbian has won the French Open three times in his career (Photo: Getty)
There is one man to blame for Djokovic ranking eighth here: Nadal.
Three triumphs have come in 2016, 2021 and 2023 with the Serbian a losing finalist on another four occasions at Roland Garros.
7. Serena Williams – US Open
Just 17 when she won her first slam at Flushing Meadows in 1999, Williams went on to win the US Open singles six times across a span of 15 years.
Nevertheless, for many she is the greatest to have ever picked up a racket, and surpassed the 100 wins milestone in New York in 2019.
The Australian Open was the scene of Federer’s first match win at a grand slam, when he beat Michael Chang in January 2000.
He passed the 100-mark in this tournament in 2020, his final outing – reaching the semis – 20 years on from his maiden appearance.
5. Chris Evert – US Open
A seven-time French Open winner but the US Open is where Evert secured 101 wins, having played that slam the most time of any majors – 19 straight appearances from 1971 to 1989.
She was an eight-time semi-finalist, three times a losing finalist and won the title six times between 1975 and 1982.
12 – Chris Evert is the female player with the fewest games dropped to secure a Grand Slam title in the Open Era (12, at the US Open 1976). Birthday.@WTA @WTA_insider @ChrissieEvert pic.twitter.com/PGb4u03Lfv
— OptaAce (@OptaAce) December 21, 2022And counting. In pursuit of grand slam No 25, this could be Djokovic’s last dance on grass.
Reaching a ton makes Djokovic the third player to do so at SW19, and with seven titles and an unbeaten run that stretched from 2018 until he lost the 2023 final, he comfortably goes down as one of this tournament’s greatest champions.
3. Roger Federer – Wimbledon
Djokovic is just one shy of Federer’s eight men’s Wimbledon singles titles, meaning it is one record the Swiss has held onto.
Two more followed in 2012 and 2017, making Wimbledon his most successful slam and the stage he will be best remembered for.
The lengthy standing ovation he received when returning after retirement in 2023 truly proved he is Centre Court’s darling.
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One hundred and twenty. No player has won more singles matches at one grand slam than Martina Navratilova.
1. Rafael Nadal – French Open
14 titles, 112-4 record
The “King of Clay” won the title in his debut appearance in 2005 and kept Federer to just the one French Open in 2009.
It is hard to imagine a player going on to leave their mark on any slam the way Nadal did at Roland Garros. He made it his own during an era where he shared the stage with two fellow legends of the men’s game.
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