According to the BBC, "The pair have long had a spiky relationship and, while there is respect and cordiality, an element of drama always appears when they meet".

[1] Medvedev and Tsitsipas first played each other in the first round of the 2018 Miami Open, when both were ranked outside of the top 50 and were 22 and 19 years old respectively.

As the chair umpire intervened, Tsitsipas quietly packed his bag to leave the court while Medvedev continued, "Look at me...

[9] Of the "bullshit Russian" remark, he has said that Medvedev had been chiding him midmatch for not apologizing for hitting the net cord, but that he "did get pissed and said what I said, which I do regret".

Medvedev said, "I do think that it's completely normal when something like this can happen, I mean, you're going to spend fifteen years on the tour and you're going to have some hot moments".

Both players received fines from the ATP because of this match, which was a rematch of their 2021 semifinal that Medvedev won in straight sets.

During a changeover in the second set, after dropping his serve with a double fault, Medvedev erupted in frustration, yelling repeatedly at the umpire, "His father can talk every point?

[14][15] In fact Tsitsipas's father Apostolos, who often gets coaching warnings at his son's matches, was shouting finable advice (in Greek) from the player's box, something tournament officials eventually laid bare in the fourth set in a "sting operation" using Greek umpire Eva Asderaki-Moore.

Though neither would ultimately make it out of the group stage, Medvedev and Tsitsipas faced off in a win-or-go-home match at the 2022 ATP Finals.

However, up a break at the end of the third set, Medvedev failed to serve out the match, partly due to an untimely pair of double faults, and Tsitsipas cruised through the decisive tiebreaker, winning 6–3, 6–7(11–13), 7–6(7–1).

[19][20] At the start of the tournament, a fan shared a video showing Medvedev and Tsitsipas passing on a narrow walkway, appearing not to acknowledge each other.

During the match, Tsitsipas got into a verbal altercation with his mother, Julia Apostoli, as she was shouting coaching advice to him in Russian.

[25] In the same interview, he went on to compliment Medvedev, saying, "The consistency and the power that he was able to put out there [...] he gave me a fresh idea of who he now is on this surface".

[25] Following their acrimonious match in Miami in 2018, Tsitsipas's mother said in an interview: "It was just a tense moment, it wasn't personal.

[28] In August 2018, after his victory over Tsitsipas at the US Open, Medvedev said, "We didn't speak after Miami ... but it's OK, I understand sometimes there are emotions on court.

"[29] After defeating Tsitsipas in Basel in October 2018, Medvedev posted a photo to his Instagram account with the caption, "Oops, I did it again".

[32][33] Medvedev has since said of Tsitsipas, "I think we respect each other as players but probably not so much on personal level ... We don't have any sort of relationship at all, I would say".

[34][35] Alexander Zverev, a generational rival of both players, said in 2019 that Medvedev and Tsitsipas have a "weird" relationship.

[47] Tsitsipas called his first win over Medvedev, at the 2019 ATP Finals, "one of the most important victories of [his] career so far" and said that it meant "more than extra" to him.

[57][58] (It was not the first time Medvedev had expressed his displeasure with Tsitsipas for receiving coaching; he made the same complaint during their 2021 Australian Open match.