ATP Rotterdam: Wawrinka defeats Raonic to make quarterfinals

Stan Wawrinka's last win over Milos Raonic came at the Rotterdam Open in 2015 -- the last time he won the tournament. Jan Kok/Soccrates/Getty Images

Three times Grand Slam champion Stanislas Wawrinka progressed to the quarterfinals of the Rotterdam Open after defeating No. 5 seed Milos Raonic 6-4, 7-6 (4) on Wednesday

Wawrinka secured the only break of the match in the third game of the opening set to edge in front, before holding to love to seal the set in the 10th game.

Following an even second set, which saw no break point opportunities, the Swiss took the tiebreak on his second match point in order to advance to the last eight.

Wawrinka will face Denis Shapovalov, the world No. 25, who comfortably defeated an in-form Tomas Berdych 6-4, 6-3.

Frenchman Gael Monfils was the first player into the quarterfinals but had to come back from a set down as he overcame Italy's Andreas Seppi 4-6, 6-1, 6-3.

In the remaining first round matches, Bosnia & Herzegovina's Damir Dzumhur recorded a big upset by defeating Australian Open semifinalist Stefanos Tsitsipas 6-4, 1-6, 7-5.

Greek No. 3 seed Tsitsipas struggled to exert authority on the lowly-ranked Dzumhur, who took the first set with an ace down the T.

Tsitsipas managed to level the scores but struggled again in the decider and, after saving match points at 4-5, eventually dropped serve to love with a forehand long to give Dzumhur the win.

Daniil Medvedev continued his fine winning run with a straight sets victory over Jeremy Chardy.

The Russian, who was crowned champion at last week's Sofia Open, defeated his French opponent 7-6 (2), 6-2 to make the last 16.

Medvedev had been forced to save the first set after squandering a comfortable advantage to set up Chardy at 5-4, but he found a timely break to restore parity then secured the crucial first set tiebreak.

After becoming home champion at the Open Sud de France last week Jo-Wilfried Tsonga also maintained his good form by beating Italy's Thomas Fabbiano 6-1, 6-4.

Hungary's Marton Fucsovics, the other finalist in Sofia, made his way into the second round with a 7-6 (4), 6-4 win over 2016 Rotterdam champion Martin Klizan.