Daniil Medvedev lost his chance at a possible second Toronto Masters title as the second seed fell 7-6 (7), 7-5 in a quarter-final to Alex de Minaur on Friday.

The 2021 champion here was riding a seven-match win streak when he ran into the 18th-ranked Aussie who defeated him for the first time in five matches last November at Paris Bercy.

De Minaur, runner-up to Stefanos Tsitsipas last weekend in Mexico, said he played cat-and-mouse with Medvedev in a thriller lasting for just over two hours.

The Aussie will compete in the first Masters 1000 semi of his career on Saturday, taking on Alejandro Davidovich Fokina after the Spanish outsider posted a 6-4, 6-2 defeat of American Mackenzie McDonald.

“I had to play my best tennis,” De Minaur said, “It’s been a great week for me so far.

“Beating Medvedev last year gave me the confidence for this match.

“It’s always a complete chess match between us, we’re both adaptable and can play many styles of tennis.

“He brings out the best in me, The way I played today was the best style of tennis that I could produce.”

Medvedev was weighed down by 44 unforced errors in defeat.

De Minaur hung tough in the opener, saving three Medvedev set points before converting on his own first chance.

The unseeded threat then took victory into the final four off a Medvedev double-fault.

Medvedev lost for only the third time this season at a Masters event,

Davidovich Fokina needed 97 minutes and three match points to defeat Mackenzie, who beat Rafael Nadal at the Australian Open in January.

The number 37 Spaniard played the 2022 Monte Carlo, his first at the elite level; he reached the Toronto quarters with a third-round defeat of world No. 5 Casper Ruud.