Stefanos Tsitsipas battled back from a set down to defeat Karen Khachanov in a three set epic and advance to the semi-finals of the ABN AMRO World Tennis Tournament in Rotterdam.
Gruelling rallies were the story of the match, as both players looked to dictate the points with their powerful groundstrokes, with Tsitsipas ultimately winning 4-6 6-3 7-5.
Tsitsipas managed to break the Russian, who had not lost serve in his two previous matches, in his opening service game.
A time violation warning was then given to Tsitsipas in the following game by umpire Fergus Murphy, a game in which Khachanov broke straight back with a brilliant backhand down the line to win it.
Khachanov broke again at his next opportunity, displaying his defensive ability to extend many of the rallies, many of which ending with a Tsitsipas error.
The 24-year-old Russian did not let this advantage slip from that point in the first set, facing no further break points and taking the set 6-4 on his fourth set point. This was the first set that Khachanov had won against 22-year-old Tsitsipas in his career, with the Greek winning their two previous matches in straight sets.
The second set started in a similar fashion to the first, with Tsitsipas dominating the opening stages and gaining an early break thanks in part to some loose errors from Khachanov.
On this occasion, despite having to save a break point, Tsitsipas was able to consolidate his break and take firm control of the set.
Khachanov’s extremely high level play that was evident throughout the first set deserted him in the second, with Tsitsipas capitalising fully on his lapse in form, at one stage having a 5-0 lead.
That 5-0 advantage was shortened to 5-3 but Tsitsipas held his nerve, successfully serving out the set at the second time of asking to win it 6-3.
Both players showed their intent and desire at the beginning of the third set, with Khachanov battling through a tense opening game to hold serve, managing to avoid giving Tsitstipas yet another early advantage.
Khachanov was able to get the first break of the final set, taking his opportunity at the third time of asking to take a 3-1 lead.
The drama continued in the following game, however, as what looked like a routine volley was missed by Khachanov when facing break point, which allowed Tsitsipas to break back.
The players exchanged holds until Tsitsipas administered the final blow of what was a brutal match, which lasted over two and a half hours, as he broke the Khachanov serve and then held his own to take the third set 7-5.
Tsitsipas improves his head-to-head record against Khachanov to 3-0, but due to the young age and tremendous talent of the two players there will likely be many more meetings between them on big stages.
He will play the victor of the upcoming match between Andrey Rublev and Jeremy Chardy, currently holding a head-to-head lead over both of his potential opponents (3-2 against Rublev and 2-1 against Chardy).
On the other side of the draw Borna Coric will meet Kei Nishikori and Marton Fucsovics will take on Tommy Paul for the other two spots in the semi-finals.
Tsitsipas is back in action later today on the doubles side, where he and his brother, Petros, will be playing against Henri Kontinen and Edouard Roger-Vasselin in the second round. The doubles event has added motivation for Tsitsipas, who said he will donate €3,000 to Mazi gia to Paidi (Together For Children), a Greek foundation, for every doubles match he wins in Rotterdam.
As the second seed, and the highest seeded player remaining in the singles event, Tsitsipas will be the favourite to take home the trophy on Sunday and win his sixth career title.