Canadian teenager Denis Shapovalov delighted his home fans when he battled from a set down to record a stunning upset victory over top seed Rafael Nadal in the third round of the Rogers Cup on Thursday.
The lanky wild card kissed the Montreal court after completing a rousing 3-6, 6-4, 7-6(4) triumph as the 18-year-old became the youngest player to ever reach the quarter-finals of an ATP Masters 1000 event.
The early exit also denied world number two Nadal a chance to take over from the absent Andy Murray at the top of the rankings, a position the Spaniard would have regained for the first time since 2014 had he advanced to the semi-finals.
Shapovalov showed no sign of nerves in their first ever meeting, the left-hander playing the more aggressive tennis by utilising his huge forehand on roundhouse swings and frequently attacking the net.
The teenager's quixotic bid looked doomed in the third set tiebreaker when he fell 3-0 behind but the world number 143 refused to buckle and only coughed up one more point in the decider.
As a reward for his unlikely victory, the 2016 Wimbledon junior champion will next face 29-year-old Frenchman Adrian Mannarino in the quarter-finals on Friday.
Federer drops a set in win against Ferrer
Elsewhere, world number three Roger Federer dropped his first set since June but the Swiss recovered to dispatch Spaniard David Ferrer 4-6 6-4 6-2 in their last 16 meeting.
Federer was sloppy from the outset on centre court, sending routine forehands wide and providing the underdog Ferrer with early break opportunities in the Montreal encounter.
Ferrer capitalised by winning the opener to end Federer's streak of 32 consecutive sets won, a record that dates back to his defeat to Tommy Haas at the Stuttgart Open on June 14.
"He had a good start, I had a better finish," Federer told reporters after the match.
Frustration boiled over for the Australian Open and Wimbledon champion in the second set after he misfired with an overhead smash.
Federer, who turned 36 this week, responded by hitting a ball into the stands, earning a reprimand but no official ball abuse call from the umpire.
The outburst appeared to steady the Swiss, whose serve and overall accuracy improved as the two-hour match progressed.
Ferrer has now lost all of his 17 contests against Federer, who is also vying to take the world number one spot from the injured Murray.
Next up for Federer is a quarter-final against 12th-seeded Spaniard Roberto Bautista Agut, who defeated Frenchman Gael Monfils 4-6, 7-6(5), 7-6(2) in a marathon tussle.
In other tournament action, American Jared Donaldson lost to Diego Schwartzman 0-6, 7-5, 7-5, while his countryman Sam Querrey was thrashed 6-4 6-1 by Kevin Anderson of South Africa.
Australian Nick Kyrgios fell 6-4, 6-3 to fourth seed Alexander Zverev as the German finally claimed victory over his opponent in their third meeting of the season.
Pliskova reaches Rogers Cup quarters after Osaka retires
World number one Karolina Pliskova was dragged into a mighty battle before being granted a berth in the Rogers Cup quarter-finals when Japanese teenager Naomi Osaka retired with an abdominal injury on Thursday.
Czech Pliskova, playing her first tournament with the top ranking, was pushed into a deciding set by qualifier Osaka before the 19-year-old called for the trainer when trailing 6-2 6-7(4) 1-0 and promptly withdrew.
"She played well, especially in the second set she was fighting pretty hard, much better than the first," said Pliskova.
"I was just trying to stay in the game, the first game of the third set was very tough I didn't even know she was injured."
Pliskova, playing her first tournament since a shock second round defeat at Wimbledon, had shown signs of rust in a ragged opening win over Anastasia Pavlyuchenkova but looked more like a world number one as she swept four straight games to take the first set from 50th-ranked Osaka.
But the Japanese rallied to match the lanky Czech shot-for-shot in a gripping second set, then dominated the tiebreak.
During the changeover, Osaka told her coach that she was feeling discomfort and was told to withdraw if the pain persisted to avoid the risk of further injury.
Osaka did just that, calling for the trainer after dropping serve to open the third set.
"I think my game today was much better, especially my serve," said Pliskova, who clubbed 13 aces. "I didn't lose my serve in this match today, I'm happy with the way I was serving today."
Pliskova will need to have her serve firing on all cylinders when she meets sixth seed and former world number one Caroline Wozniacki in the last eight.
Wozniacki cruises past Radwanska
In a battle of former-Rogers Cup champions, a ruthless Wozniacki showed no mercy by sweeping past her good friend Agnieszka Radwanska 6-3, 6-1 in just 78 minutes.
The only hiccup in an otherwise polished effort against the 10th-seeded Pole came when Wozniacki was up 5-0 in the second and squandered three match points.
But the Dane closed out the match on the next chance with a stinging forehand winner.
"We've known each other since we were five and six years old so there are no secrets out there," said Wozniacki, who has reached five finals this season without winning a title.
"It is always unfortunate to play a good friend in such an early round but at the same time it is part of the game."
Czech Lucie Safarova also made the last eight by outlasting Russia's Ekaterina Makarova 6-3, 6-7(3), 6-2, while France's Caroline Garcia beat 18-year-old American Catherine Bellis 6-4 6-2.
Venus Williams stunned in third round of Rogers Cup
Seven-time Grand Slam champion Venus Williams suffered a major setback as she bowed out of the Rogers Cup after going down against Ukraine's Elina Svitolina, in the third round of the women's singles event here on Friday.
Williams, who was the oldest player in the draw, was easily dispatched by fifth-seed Svitolina 2-6, 1-6 in a third round encounter that lasted exactly an hour.
In the second career meeting between the two players, Svitolina was in a strong position from the beginning as she took a 5-0 lead over Williams in the opening set and never returned.
The Ukrainian smashed 14 winners while making just 10 unforced errors en route to her first-ever victory over Williams.
Svitolina will now lock horns with fourth-seed Garbine Muguruza in her first-ever quarterfinals at the Rogers Cup.
In another women's singles clash, third-seed Angelique Kerber of Germany was also knocked out of the tournament after suffering a 2-6, 2-6 defeat against American tennis player Sloane Stephens.
Stephens will face Czech Lucie Safarova in the quarter-finals.
Fourth seed Garbine Muguruza dispatched Ashleigh Barty of Australia 6-0, 3-6, 6-2 at their centre court meeting.