Rafael Nadal fell to a shock defeat by 18-year-old Canadian Denis Shapovalov at the Rogers Cup in Montreal.
Wildcard Shapovalov came from a set down to beat top seed Nadal 3-6 6-4 7-6 (6-4) and become the youngest player to reach a Masters 1000 quarter-final.
Nadal’s loss means Andy Murray remains world number one, but only until next week’s Cincinnati Masters, where Nadal or Roger Federer will replace him.
Federer also progressed to the last eight, with victory over David Ferrer.
The Swiss world number three, 36, came from a set behind to beat the Spaniard 4-6 6-4 6-2 and next faces Roberto Bautista Agut, also of Spain, who defeated Frenchman Gael Monfils 4-6 7-6 (7-5) 7-6 (6-2).
World number 143 Shapovalov, the 2016 Wimbledon junior champion, next plays 29-year-old Frenchman Adrian Mannarino after his stunning win over Nadal.
“He’s honestly the best player I’ve ever played in my life,” said Shapovalov, the youngest man to beat a top-two player since the 17-year-old Nadal beat Federer in 2004.