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Teenage wild card Denis Shapovalov has produced the biggest upset of his young career, taking down No. 11 seed Nick Kyrgios in the opening round of the Rogers Cup.

The 17 year old, who won the Boys’ Singles Title at Wimbledon earlier this month, made the most of his main draw opportunity to defeat the Australian 7-6(2), 3-6, 6-3 in one hour and 40 minutes.

“Nick is an incredible tennis player. He’s Top 20 in the world. Maybe even future No. 1 in the world,” Shapovalov said. “So obviously I didn’t expect to win. But like I said before, I’m just going to go fight for every point. That’s what I did. The outcome was very good today.”

Buoyed by the Toronto crowd, the young Canadian brought up match point with his 12^th ace and closed it out to book a second-round meeting with former Top 10 player Grigor Dimitrov.

“I love playing on a big stage. I love impressing people,” said Shapovalov, who requested to play on Centre Court. “It was very fun for me.”

Both players saved eight of 10 break points faced but Kyrgios was let down by 18 double faults. Shapovalov had just four.

“He’s coming off of one of the best results of his career. He has a great future,” Kyrgios said. “I’m really looking forward to seeing how he’s going to progress… He’s a top player.”

Earlier, Dimitrov produced an impressive escape to deny Japan’s Yuichi Sugita 5-7, 7-6(5), 6-4 in two hours and 29 minutes.

The Bulgarian trailed a set and a break and was down 3/5 in the second-set tie-break before forcing the deciding set. He landed the crucial break for 3-2 in the third and sealed it on his first match point.

American Sam Querrey also advanced to the second round on Monday, winning almost 90 per cent of his first-serve points to beat Canadian wild card Frank Dancevic 7-6(5), 6-4 in an hour and 27 minutes.

Twelfth seed Bernard Tomic started his sixth consecutive appearance at the Rogers Cup with a 6-4, 7-6(1) win over Colombian qualifier Alejandro Gonzalez on Monday, day one of the ATP World Tour Masters 1000 tournament in Toronto.

Tomic was perfect at the net – 12/12 – and hit 34 winners to help balance out his 41 unforced errors. “[Gonzalez] played two good matches in qualifying and he had a bit of momentum… so it was not easy for me,” Tomic said.

The Aussie’s best run at the Rogers Cup came last year when he reached the third round (l. to Tsonga).

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“I feel like here’s a good chance for me,” Tomic said. “I really have to focus and really go for my shots and relax if I want to make a quarter or semi.”

The 6’5” 23-year-old next will face Canadian wild card Steven Diez. The 25 year old, No. 192 in the Emirates ATP Rankings, earned the “biggest win” of his career by upsetting Brit Kyle Edmund 3-6, 6-3, 6-2. Diez won four of his 10 break points to land his first win at an ATP World Tour Masters 1000 tournament.

“I’m really happy. I still don’t have a lot of words to describe what just happened. I know I played pretty well,” said Diez, who enjoyed the support from relatives at the match.

He had been 0-4 in Rogers Cup qualifying (2010, 2011, 2013, 2014).

South African Kevin Anderson prevailed against Serbian Viktor Troicki 7-6(4), 6-3 to move into the second round. The 30-year-old right-hander lost only five points on his first serve (29/34) and feasted on Troicki’s second offering, winning almost 60 per cent (10/18) of Troicki’s second-serve points.

The 2014 Rogers Cup quarter-finalist next will face sixth seed Dominic Thiem, who will be going for his first Rogers Cup victory. Anderson leads their FedEx ATP Head2Head series 4-0, including a three-set win at the Masters 1000 tournament in Paris last year.

Russian Mikhail Youzhny set-up a second-round contest against second seed Stan Wawrinka. The Moscow native beat Frenchman Stephane Robert 6-3, 7-6(6). The 34-year-old Youzhny, No. 61 in the Emirates ATP Rankings, leads his FedEx ATP Head2Head series against Wawrinka 3-2, including a win the last time they played (2010 US Open).

Jack Sock, the 16^th seed, won an all-American battle to advance to the second round. Sock dismissed Denis Kudla 6-2, 6-2 in an hour and eight minutes. The 23 year old will face compatriot Donald Young or Alexandr Dolgopolov of the Ukraine in the second round.