Milos Raonic falls to 81st seed at Shanghai Masters

Four American players pulled off upsets at the Shanghai Masters on Monday. A fifth wasn't so lucky. Sam Querrey, Mackenzie McDonald, Bradley Klahn and Taylor Fritz all posted wins in the first round of the tournament, while Frances Tiafoe lost his match.

'Definitely my biggest win to date,' says American Mackenzie McDonald

Canada's Milos Raonic was ousted in the first round of the Shanghai Masters on Monday, dropping a 6-3, 5-7, 6-3 decision to 81st-ranked Mackenzie McDonald of the United States. (Koji Watanabe/Getty Images/File)

Perhaps the most surprising win Monday at the Shanghai Masters came from 81st-ranked Mackenzie McDonald of the United States, who defeated 14th-seeded Milos Raonic 6-3, 5-7, 6-3.

"Definitely my biggest win to date," said McDonald, a qualifier into the main draw. "I thought I played great tennis and I could feel all the improvements I've had over the last few months and was happy I could put it together tonight."

It was the second meeting between the two after Canada's Raonic won their fourth-round encounter at Wimbledon in four sets in July.

Watch Mackenzie McDonald complete his victory over Milos Raonic:

Canadian Milos Raonic was knocked out by American Mackenzie MacDonald on Monday in China. 1:28

In all, four American players pulled off upsets on the day. A fifth wasn't so lucky.

Sam Querrey, Bradley Klahn and Taylor Fritz all posted wins in the first round of the tournament, while Frances Tiafoe lost his match.

No. 10 Tsitsipas advances

Klahn, also a qualifier and making his first appearance in Shanghai, defeated Nick Kyrgios 4-6, 6-4, 6-3. The talented but erratic Kyrgios has played in Shanghai four times with his best showing being two second-round finishes.

Querrey upset ninth-seeded Diego Schwartzman 6-3, 6-4, while Fritz beat Robin Haase 6-3, 7-6 (3). The pair will face each other in the next round.

Tiafoe, however, lost to Matthew Ebden 3-6, 6-4, 6-3.

Also, 10th-seeded Stefanos Tsitsipas beat Gael Monfils 7-6 (4), 4-6, 6-4 and 13th-seeded Borna Coric of Croatia defeated wild-card entry Stan Wawrinka 4-6, 6-4, 6-3.

The 20-year-old Tsitsipas is one of the fastest rising players on tour. He started the season ranked No. 91 and is currently sitting at No. 15.

"I have improved a lot since last year physically, mentally," said Tsitsipas, who was a qualifier last year but is seeded this year. "My game has changed. I am more aggressive now. I'm actually stronger."

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