Eight and a half years ago in Miami, a 22-year-old Daniil Medvedev and a 19-year-old Stefanos Tsitsipas, both outside the top 50, played a first-round match that ended with the Russian shouting at the Greek from his bench. On Wednesday, the same two men meet in the Shanghai Masters round of 16 for the 16th time. Medvedev, the No. 5 seed, leads their head-to-head 10-5. Tsitsipas, ranked No. 43, won the last one, in Doha in February.
The match is a rivalry renewed, but it has a different feel from most of the previous 15. In the early years it was among the most combustible matchups on tour, with insults at the net, a coaching "sting operation," a fine for each player and a famous umpire meltdown. Today the two seem to tolerate each other, and Tsitsipas has said he respects Medvedev more than he did.
Both arrive in Shanghai with their own storylines. Medvedev won Hangzhou two weeks ago for his 24th title, then was disqualified from the Beijing semifinal against Novak Djokovic on October 5 after a ball he hit in frustration struck a spectator. He called it an accident. Tsitsipas reached his 400th career win here on Saturday and rallied from a set down to beat Taylor Fritz on Monday. Here is where each stands before the match.
Daniil Medvedev
Stefanos Tsitsipas
Age
30
28
Ranking
No. 6
No. 43
Career titles
24
13
Grand Slam titles
1 (2021 US Open)
0
Career-high ranking
No. 1
No. 3
Career wins
458
400
2026 titles
3 (Brisbane, Dubai, Hangzhou)
1 (Gstaad)
Miami 2018: the match that lit the fuse
Medvedev won their first meeting 2-6, 6-4, 6-2, but the scoreline was a footnote. The two exchanged barbs during the match, and afterward Medvedev, furious, shouted at Tsitsipas from his bench and then at the chair umpire. His complaints centered on a long bathroom break by Tsitsipas, even though Medvedev had taken one too, and on the Greek not apologizing for a net-cord point. At one point he called him a small kid who did not know how to fight.
Tsitsipas has said that some words were exchanged at the net, including a remark about a "Russian" that he has said he regrets. He later described the post-match atmosphere as overly hostile. His mother tried to cool things down, saying the moment was tense but not personal, and that Medvedev's parents had been at the family's house for dinner two weeks earlier. That detail helps explain why the rivalry has always felt more like a clash of personalities than a feud between families.
The rivalry also started with a one-sided run. Medvedev won the first five meetings, including the 2018 US Open and the Basel quarterfinals that autumn, where he celebrated on Instagram with an "Oops, I did it again" caption. After the US Open, he also mentioned that Tsitsipas had blocked him on the platform.
#
Year
Tournament
Round
Surface
Winner
Score
1
2018
Miami Open
R128
Hard
Medvedev
2-6, 6-4, 6-2
2
2018
US Open
R64
Hard
Medvedev
6-4, 6-3, 4-6, 6-3
3
2018
Basel
QF
Indoor hard
Medvedev
6-4, 3-6, 6-3
2019: "Not friends" and a first win
By 2019, both players were openly lukewarm about each other. Medvedev said they had no relationship and were definitely not friends. Tsitsipas said their chemistry was not the best on tour and that they would not be going to dinner together. Alexander Zverev, a contemporary of both, called the dynamic "weird."
The comments got sharper after Medvedev beat Tsitsipas in the Shanghai semifinals that October, 7-6(5), 7-5, on his way to the title. Tsitsipas called his rival's game "so boring," and Medvedev later hit back. It was the fifth win in five meetings for the Russian.
Then Tsitsipas finally broke through. At the 2019 ATP Finals in London, he won their sixth meeting 7-6(5), 6-4 without facing a break point and went on to win the title.
#
Year
Tournament
Round
Surface
Winner
Score
4
2019
Monte-Carlo
R16
Clay
Medvedev
6-2, 1-6, 6-4
5
2019
Shanghai
SF
Hard
Medvedev
7-6(5), 7-5
6
2019
ATP Finals
RR
Indoor hard
Tsitsipas
7-6(5), 6-4
2021: respect, the Slam years and a thaw
The rivalry reached its peak in the Slams. At the 2021 Australian Open semifinals, Medvedev won 6-4, 6-2, 7-5, and Tsitsipas conceded that the Russian outsmarted him, saying that Medvedev "tricks you" and walking back his earlier "boring" comment. Medvedev had complained during that match that Tsitsipas's father, Apostolos, was talking too much from the stands.
Four months later, Tsitsipas got his revenge at Roland Garros. He beat Medvedev 6-3, 7-6(3), 7-5 in the quarterfinals, and Medvedev called it the match of the day and said he had not expected such a great level. Tsitsipas praised him as one of the best on tour.
The relationship thawed, too, after both played on the same Laver Cup team in September 2021. Tsitsipas said it "kind of got better," though he also called Medvedev's game one-dimensional shortly before the event. For a time, it seemed the rivalry had matured.
#
Year
Tournament
Round
Surface
Winner
Score
7
2021
Australian Open
SF
Hard
Medvedev
6-4, 6-2, 7-5
8
2021
Roland Garros
QF
Clay
Tsitsipas
6-3, 7-6(3), 7-5
January 2022: the Melbourne meltdown
It did not last. In the 2022 Australian Open semifinals, Medvedev lost his composure during the second set after dropping serve with a double fault and began shouting repeatedly at chair umpire Jaume Campistol, asking why Tsitsipas's father was allowed to talk after every point. The ATP fined him A$12,000 for unsportsmanlike conduct.
He was not entirely wrong. Tournament officials set up a sting operation, using the Greek-speaking umpire Eva Asderaki-Moore to listen in, and Tsitsipas received a coaching warning and a A$5,000 fine. Medvedev won the match and later admitted he had been "out of my mind" in that moment. Tsitsipas called the outburst shameful and said Medvedev was not the most mature person.
After the victory (7-6(5), 4-6, 6-4, 6-1), Medvedev said it all started in Miami and that every match against Stefanos was special. It was the single most heated moment in their history, and the match's drama was driven by the people in the player's box as much as by the players.
2022–2023: Cincinnati, Turin, Rublev and Rome
Tsitsipas turned the tables on court in the second half of 2022. At the Cincinnati Masters semifinals he beat Medvedev 7-6(6), 3-6, 6-3, coming to the net often to disrupt the Russian's deep defense. At the ATP Finals in Turin, he won a winner-take-all group match 6-3, 6-7(11), 7-6(1), after Medvedev saved three match points in the second-set tiebreak and then failed to serve out the match in the third.
The off-court friction came back, this time through Andrey Rublev, Medvedev's close friend and the godfather of his daughter. After losing to Rublev in Turin, Tsitsipas said Rublev had won with the few tools he had, then apologized. Medvedev addressed it in his Dubai victory speech in March 2023, without naming him.
They met in the Rome semifinals in May 2023 and Medvedev won 7-5, 7-5. The match came with its own sideshow: Tsitsipas got into an argument with his mother, Julia Apostoli, who was shouting advice in Russian, and she moved to the stands behind Medvedev's box. Medvedev then celebrated by dancing, a reference to Tsitsipas's Cincinnati celebration. Tsitsipas took it in stride and said he had done the same months earlier.
#
Year
Tournament
Round
Surface
Winner
Score
9
2022
Australian Open
SF
Hard
Medvedev
7-6(5), 4-6, 6-4, 6-1
10
2022
Cincinnati
SF
Hard
Tsitsipas
7-6(6), 3-6, 6-3
11
2022
ATP Finals
RR
Indoor hard
Tsitsipas
6-3, 6-7(11), 7-6(1)
12
2023
Rome
SF
Clay
Medvedev
7-5, 7-5
13
2023
Vienna
SF
Indoor hard
Medvedev
6-4, 7-6(6)
2024: Shanghai, the shot clock and a truce
By 2024, the rivalry had softened. In Shanghai, ahead of their 14th meeting, Tsitsipas said he respected Medvedev more than before. The heated moments, he said, had resolved themselves over time, and the two had been able to speak about why they happen. It was the clearest sign yet that the bitterness had faded.
Medvedev won that match 7-6(3), 6-3 to extend his lead to 10-4. The drama came from Tsitsipas and the chair umpire. After a time violation in the second set, the Greek complained that he was being singled out, lost his serve, then refused to receive the next game until a tournament supervisor came onto the court. The target was the umpire, not Medvedev.
Then the rivalry went quiet. They did not play for 16 months, one of the longest gaps of their careers, and Tsitsipas's form dipped. A back injury marred 2025, which he ended 22-20 and ranked No. 34. Medvedev, too, had an unusually poor year before recovering in 2026.
Looking back, the tension had a clear arc, from open hostility in 2018 to a respectful truce six years later:
When
Where
What happened
March 2018
Miami
Post-match shouting at the bench over a bathroom break and a net-cord point
Aug.–Oct. 2018
US Open, Basel
Silence after Miami, a blocked Instagram account and an "Oops, I did it again" post
Oct. 2019
Shanghai
Tsitsipas calls Medvedev's game "so boring" after the semifinal
Jan. 2022
Australian Open
Medvedev's umpire meltdown over coaching; fines of A12,000andA5,000
Nov. 2022
Turin
Tsitsipas says Rublev won with the "few tools" he has; later apologizes
Mar. 2023
Dubai
Medvedev answers the Rublev comment in a victory speech, without naming him
May 2023
Rome
Tsitsipas argues with his mother in the stands; Medvedev dances after the win
Oct. 2024
Shanghai
Tsitsipas feuds with the umpire over a time violation, not with Medvedev
2026: Doha turns the tables
The two met again in Doha in February. Tsitsipas had lost three straight against Medvedev without winning a set, and he came in ranked No. 33 against the world No. 11. He won 6-3, 6-4 with a serving clinic, closing points at the net and recording only his second win over a top-20 opponent since the end of 2024. It was his first win over Medvedev since 2022.
Eight months on, the two are in very different places. Medvedev has won three titles in 2026 (Brisbane, Dubai and Hangzhou), is ranked No. 5, and was on a winning streak until the Beijing default. Tsitsipas has fought back from a bad stretch, winning Gstaad in July and climbing from No. 87 to No. 43, and he says he wants to return to the top 30 by year's end.
#
Year
Tournament
Round
Surface
Winner
Score
14
2024
Shanghai
R16
Hard
Medvedev
7-6(3), 6-3
15
2026
Doha
R16
Hard
Tsitsipas
6-3, 6-4
The matchup, by the numbers
Medvedev's lead is decisive but not lopsided, and it has changed over time. After five wins in a row to open the rivalry, Tsitsipas won four of the next eight. Since then, Medvedev has taken three of the last four meetings, with Doha the exception.
Medvedev has had the edge on serve and in long matches. He has won 78% of first-serve points against Tsitsipas's 74%, and 56% of second-serve points to 50%. Eight of their 15 meetings ended in straight sets, and five went the distance. Tsitsipas's wins have come when he served well and used the net, as he did in Cincinnati in 2022 and again in Doha.
Medvedev
Tsitsipas
Overall
10
5
Hard courts
8
4
Clay
2
1
Grand Slams
3
1
Masters 1000
5
1
ATP 500
2
1
ATP Finals
0
2
Best-of-three matches
7
4
Best-of-five matches
3
1
Deciding sets
3
2
Tiebreaks
5
4
What to watch on Wednesday
The easy prediction is Medvedev: he leads 10-5, he is a better and more consistent hard-court player this year, and he can defend Tsitsipas's best shots. But the last meeting is a reminder that the rivalry is less one-sided than the head-to-head suggests. Tsitsipas beat him in straight sets in February, and he arrives in Shanghai having already knocked out two seeded players, including Fritz, with a serve that has been his best weapon.
The match will also test two players who have both had very different weeks. Medvedev is coming off the Beijing default and a two-week run of title and disappointment. Tsitsipas is playing with rare confidence and described his win over Fritz as a statement. He has called Medvedev a great defender who can counter his best shots, which is exactly what he will have to solve.
The rivalry has calmed as both players have matured. They are no longer 19 and 22 and in a hurry to prove something. There is likely to be less shouting this time. But the history means that, in a Masters 1000 round of 16, nobody should be surprised if it still comes with a little drama.
Cristhián Ávila is a tennis journalist based in Santiago, Chile, and has been part of the TennisUpToDate team since early 2023. He covers the ATP and WTA Tours as well as all four Grand Slams, producing breaking news, match reports, analysis, and regular liveblogs from major tournaments.
His reporting combines statistical analysis with clear explanation, helping readers understand tactical developments, player form, and broader storylines across the tour. Working fluently in both Spanish and English, Cristhián collaborates with an international editorial team and contributes to comprehensive global coverage. As part of his work, he has conducted interviews and media interactions with leading figures in the sport, including Caroline Wozniacki and John McEnroe.
In his journalism, Cristhián places strong emphasis on careful sourcing, editorial accuracy, and updating articles promptly when new, verified information becomes available. His coverage is grounded in research, context, and direct engagement with professional tennis.