Top 5 Grand Slam men's singles matches of 2019

#4 Roland Garros 4th Round: Stan Wawrinka beat Stefanos Tsitsipas 7-6(6) 5-7 6-4 3-6 8-6

Tsitsipas looks disconsolate after losing an epic-five setter to Wawrinka

Fresh off a maiden Grand Slam semifinal at the Australian Open earlier in the season, Stefanos Tsitsipas beat Maximilian Marterer, Hugo Dellien and Filip Krajinovic at Roland Garros to reach the second week of a Major for the second time in his young career.

A battle of the single-handers ensued in Tsitsipas' first-ever match-up against 2015 winner Stan Wawrinka in the fourth round.

Tsitisipas was slower off the blocks, sending down a double fault on set point down to concede the opener after a keenly fought tiebreak. But the young Greek responded with three breaks of the Wawrinka serve in the second set to make it one set apiece.

Wawrinka survived three break points in the third set, going 22/27 for the match, as he broke Tsitsipas to grab a 2 sets to 1 lead. Tsitsipas responded with an early break in the fourth to ensure that his first-ever encounter with the former champion would go the distance.

In a pulsating deciding set, Wawrinka saved three break points to hold for 6-5. Serving to stay in the match, Tsitsipas saved the first match point but soon a second ensued for the Swiss.

Venturing to the net, the young Greek inexplicably let a Wawrinka sliced backhand go past him, in the hope that it would sail long - only to agonizingly see the ball skim the line.

With the chair umpire ruling the point in Wawrinka's favour, a gladiatorial five-hour battle royale drew to a close. With the win, Wawrinka booked a quarterfinal rematch with his good friend and compatriot Roger Federer.

Tsitsipas was left to wonder what might have been had he opted to make what looked like a pretty makable volley on Wawrinka's second match point.