Novak Djokovic and Marin Cilic made tennis history with their second-round match at the Shanghai Masters.
The storied rivals met for the 22nd time on the ATP Tour and for the first time since a meeting in the Tel Aviv final in 2022.
Djokovic has dominated their head-to-head since their first meeting in 2008, winning 19 of their meetings.
The two men set an ATP Tour record during their second-round irrespective of the final match result in Shanghai.
Novak Djokovic vs Marin Cilic is the oldest ATP 1000 match in history
Djokovic and Cilic are the elder statesmen of the sport in 2025, having dominated the game for much of the 2000s and 2010s.
The Serbian is one of the greatest players the sport has ever seen and the most storied Grand Slam champion with 24 major titles to his name.
Cilic, meanwhile, impressively picked up his sole Grand Slam win at the 2014 US Open at the height of the Big Four’s domination.
The pair’s match in the Shanghai Masters second-round saw the two men compete in the oldest match in ATP 1000 event history.
Cilic and Djokovic have a combined age of 75 years and 139 days with both men continuing to impress in the twilight of their careers.
Revisiting Marin Cilic’s only wins against Novak Djokovic
Djokovic and Cilic’s head-to-head weighs incredibly in the favour of the 24-time Grand Slam champion, but the Croatian’s wins came back-to-back.
Cilic knocked Djokovic out of the quarter-finals of the ATP Paris Masters in 2018, before losing to John Isner in the last four.
The Croatian also defeated Djokovic in the final of Queen’s in London in 2018 to lift one of his 21 career titles.
However, Djokovic got the last laugh over his great rival as he lifted the Wimbledon title weeks later, while Cilic was dumped out in the second round at the hands of Guido Pella.
