Medvedev failed to convert three match points in the second set after taking a 5-2 lead. An hour later the Russian was still playing, and on a humid afternoon with temperatures in the mid 80s, he paid a price.
Shapovalov, who enjoyed a winning debut in Dubai thanks to a 6-1, 6-3 second-round success over German big-server Jan-Lennard Struff on Tuesday, says being confined to a hotel room at every tournament due to the Covid-19 restrictions in place can take a mental toll on the players.
Zverev had to dig deep for his 6-7 (5/7), 6-3, 7-6 (7/4) win to seal the tie, but gained valuable court time ahead of another crack at a first Grand Slam trophy at the Australian Open starting next week.
Cologne Championship: Zverev advances to quarter-finals after beating Millman; Auger-Aliassime beats Gerasimov
Canada's Felix Auger-Aliassime recovered from losing the first set to seal a 4-6, 7-6 (7/2), 7-6 (7/4) second-round win over Egor Gerasimov of Belarus late on Wednesday.
US Open 2020: Borna Coric stages epic comeback to stun Stefanos Tsitsipas; Novak Djokovic sails into last 16
Croatia's 27th seed Borna Coric staged a remarkable Houdini act to stun fourth seed Stefanos Tsitsipas in a 4hr 36min late-night thriller.
Western & Southern Open: Naomi Osaka withdraws from semi-final in protest, tournament 'paused' for a day
Naomi Osaka tweeted that as a Black woman, she feels compelled to pull out of the tournament to put a focus on police shooting Black people.
Dubai Tennis Championships: Novak Djokovic bolts into semi-finals; Stefanos Tsitsipas comes from set down to beat Jan-Lennard Struff
In all, Djokovic sent down 19 winners to Khachanov’s nine, won 89% of his first serve points, nine of 11 forays to the net, and wrapped up the one-sided affair in just 66 minutes.
Australian Open 2020: Dominic Thiem's early arrival in Australia helping his confidence, feels his coach Nicolas Massu
An acclaimed clay-court player and a two-time runner-up at Roland Garros, Thiem won three of his five titles in 2019 on hard court and also picked up his first hard court win against the Serb at the ATP Finals.
Australian Open 2020: Novak Djokovic struggles past Jan-Lennard Struff to enter second round; Ash Barty beats Leisa Tsurenko
Playing against an opponent he defeated both times in straight sets in the past, Djokovic lost his serve four times in the match on Rod Laver Arena, where he beat Rafa Nadal in last year’s final to pick up a seventh Australian Open title.
Australian Open 2020 Draw: Novak Djokovic, Roger Federer in same half; Serena Williams, Naomi Osaka, Caroline Wozniacki in same quarter
Australian Open gets underway on 20 January in Melbourne with the country still reeling from dangerous air quality in the aftermath of the bushfires. The draw was conducted on 16 January.
ATP Cup 2020: Nick Kyrgios produces aces masterclass, Alexander Zverev fizzles against Alex de Minaur as Australia win
Kyrgios opened and closed his 6-4, 7-6 (4) win over Jan-Lennard Struff on Friday in Brisbane with booming, high-value serves — including a second-service ace down the middle to close it out.
ATP Paris Masters 2019: Daniil Medvedev suffers first defeat since US Open final; defending champion Karen Khachanov bundled out
Medvedev, who had reached six successive finals, looked in control when he took the first set but he ultimately paid for failing to convert 14 of the 15 break points he carved out
Shanghai Masters 2019: Andrey Rublev upsets 12th seed Borna Coric in straight sets; Matteo Berrettini through to second-round
It was a 36th win of the season for the 11th-seeded Berrettini who has now won 30 of those matches since defeating Struff on 22 April
Wimbledon 2019, singles round-up: Rafael Nadal, Serena Williams storm into fourth round; Fabio Fognini ousted
Serena Williams, Ashleigh Barty and Petra Kvitova eased into the fourth round while Tennys Sandgren stunned 12th-seeded Fabio Fognini in the third round.
French Open 2019: Novak Djokovic sets Roland Garros last-eight record as Simona Halep reaches quarter-finals with 45-minute thrashing
Novak Djokovic will now face either ninth-seeded Italian Fabio Fognini or fifth seed Alexander Zverev in what will be his 13th appearance overall in the quarter-finals at French Open
Madrid Open 2019: Roger Federer posts convincing win over Richard Gasquet on return to clay after three-year absence
Roger Federer shook off a brief bout of pre-match jitters as he returned to clay after three years, posting a win over Richard Gasquet at the Madrid Open.
Barcelona Open: Rafael Nadal inches closer to ATP record after seeing off Jan-Lennard Struff in quarter-finals
Rafael Nadal held off Jan-Lennard Struff 7-5, 7-5 in the Barcelona Open quarter-finals on Friday to move closer to setting an ATP record as the first player to win the same event 12 times.
Monte Carlo Masters: Germany's Jan-Lennard Struff upsets birthday boy Denis Shapovalov in opening round
Canadian Denis Shapovalov endured a birthday to forget as he suffered a 5-7, 6-3, 6-1 defeat to unseeded German Jan-Lennard Struff in the opening round of Monte Carlo Masters on Monday.
Indian Wells Open: Alexander Zverev suffers defeat against Jan-Lennard Struff; Novak Djokovic's match rained out
Ailing World No 3 Alexander Zverev crashed out of the ATP Indian Wells Masters, where Novak Djokovic's third round match was suspended by rain with one game completed.
Sofia Open: Stefanos Tsitsipas downs Germany's Jan-Lennard Struff in straight sets to reach quarter-finals
Stefanos Tsitsipas, who stunned Roger Federer on his way to a shock appearance in the Australian Open semi-finals, made a winning return to action on Thursday when he defeated Germany's Jan-Lennard Struff 7-6 (7/5), 6-4 to reach the Sofia Open quarter-finals