Denis Shapovalov breaks serve three times in his four-set loss against Novak Djokovic.

Denis Shapovalov falls short in four sets against World No. 1 Novak Djokovic at the Australian Open.

Denis Shapovalov celebrates reaching the Australian Open third round by beating Taro Daniel on Thursday.

Denis Shapovalov beats Pablo Andujar in straight sets at the Australian Open on Tuesday.

Seventh seed Denis Shapovalov strikes a forehand against fellow Canadian Peter Polansky on Wednesday in Stockholm.

#NextGenATP players Denis Shapovalov, Stefanos Tsitsipas and Taylor Fritz are pursuing their maiden ATP World Tour titles in Stockholm this week.

#NextGenATP Canadian Denis Shapovalov saves one match point before eventually ousting German Jan-Lennard Struff in the Tokyo quarter-finals.

Denis Shapovalov reaches the Tokyo quarter-finals on Wednesday with a big win against Stan Wawrinka.

Denis Shapovalov celebrates beating last year's Next Gen ATP Finals champion Hyeon Chung on Monday in Tokyo.

#NextGenATP Canadian Denis Shapovalov advances to his fourth tour-level quarter-final of the season with a three-set win on Thursday.

Denis Shapovalov celebrates winning on his debut at the St. Petersburg Open tournament on Wednesday with victory over Adrian Menendez-Maceiras.

Denis Shapovalov hit 59 winners in his five-set loss to Kevin Anderson at the US Open on Friday.

Denis Shapovalov is aiming to reach the US Open Round of 16 for the second straight year.

Denis Shapovalov survives in five sets to reach the US Open third round.

Denis Shapovalov will meet Italian veteran Andreas Seppi in the second round of the US Open.

Milos Raonic levels his FedEx ATP Head2Head series with Denis Shapovalov at 1-1.

Denis Shapovalov records his 25th match win of the year with yet another hard-fought victory over Kyle Edmund on Tuesday in Cincinnati.

Denis Shapovalov reaches the third round of the Rogers Cup for the second consecutive year on Wednesday in Toronto.

Denis Shapovalov reacts after beating Jeremy Chardy in straight sets in the first round in Toronto.

Denis Shapovalov makes his return to Toronto as the top Canadian.

Denis Shapovalov rebounds from 1-4 down in the third set to beat Daniil Medvedev in the Citi Open second round.

Denis Shapovalov made his Eastbourne debut a successful one by battling past Jared Donaldson on Wednesday.

Denis Shapovalov wins just his second grass-court match in a hard-fought clash over Jared Donaldson on Wednesday in Eastbourne.

Third seed Denis Shapovalov will meet Jared Donaldson in the second round of the Nature Valley International.

In his first Grand Slam as a seeded player, #NextGenATP Canadian Denis Shapovalov loses in the second round against German Maximilian Marterer.