Canadian teenager Felix Auger-Aliassime has recorded one of the biggest wins of his career.

The No. 8 seed from Montreal upset top-seeded Stefanos Tsitsipas of Greece 7-5, 6-2 in the quarterfinals of the Queen’s Club grass-court tournament on Friday.

Tsitsipas, ranked sixth in the world, marks the highest-ranked player the 21st-ranked Auger-Aliassime has beaten in his career.

Auger-Aliassime, 18, also beat Tsitsipas in Indian Wells, Calif., earlier this year when the latter player was ranked 10th.

Auger-Aliassime will play Feliciano Lopez after the unseeded veteran from Spain beat No. 6 seed Milos Raonic of Thornhill, Ont., 4-6, 6-4, 7-6 (5) later Friday.

The 113th-ranked Lopez, 37, won Queen’s Club in 2017.

The win against Tsitsipas was Auger-Alaissime’s fifth in as many matches against the Greek star dating back to their junior days.

“Whenever I step on court with him, I believe I can win and that’s obviously a big plus,” Auger-Aliassime told the ATP Tour.

Auger-Aliassime fought off seven break-point chances for Tsitsipas and won 77 per cent of his first-serve points.

Auger-Aliassime has not been broken in three matches this week, holding serve in all 38 games. He has saved nine break points.

The Canadian is looking to make his fourth ATP Tour final of the season. He lost last week to Italy’s Matteo Berrettini in the final of the Stuttgart Cup, Auger-Aliassime’s tour-level grass-court debut.

Auger-Aliassime is the youngest semifinalist at Queen’s Club, a Wimbledon tune-up, since Lleyton Hewitt recorded the feat at age 18 in 1999.

The Raonic-Lopez match couldn’t have been much closer. The Canadian won 101 points, while Lopez took 99.

Raonic fought off one match point on Lopez’s serve in the tiebreak, but then hit a shot into the net to end it.

Raonic was returning after dropping out of Stuttgart with a back injury prior to a semifinal against Auger-Aliassime.

— With files from Global’s Alessia Simona Maratta

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