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Canada’s Denis Shapovalov was eliminated from the Madrid Open on Tuesday after a 6-1, 3-6, 6-2 loss to former No. 1 Andy Murray in second-round action.

Shapovalov put himself in an early hole as he struggled with his command in a wild first set. He won just 48 per cent of his service points and managed to win just seven out of 25 points on return.

Murray broke Shapovalov twice on three chances in the opening set, and the Scotsman defended the only break point he faced.

Murray, a two-time Madrid Open champion, had the chance to take control of the second set at 2-2 with a chance for a break. But he was unable to convert and Shapovalov roared back to force a deciding set.

Shapovalov, seeded 14th in Madrid, couldn’t build on his second-set success and Murray put the game away with his fourth break of the match.

Murray will next face top seed Novak Djokovic.

Eighth-seed Félix Auger-Aliassime of Montreal, who opens his tournament Wednesday against Chile’s Cristian Garin, is the last Canadian remaining in singles competition.

Bianca Andreescu, the last Canadian left on the women’s side, lost 7-6, 6-1 to American Jessica Pegula in a third-round match earlier Tuesday.

Pegula, the tournament’s 12th seed, had Andreescu on her heels for most of the match, winning 57.1 per cent of the total serve points available to her.

Andreescu, the 2019 U.S. Open champion, fought off 14 of 17 break points in the opening set before being broken three times on four attempts in the decisive second set.

Andreescu entered the clay-court tournament with a world ranking of 111.

She reached a career-high ranking of No. 4 in October, 2019, thanks to her breakout season that saw her win prestigious events in Toronto and Indian Wells, Calif., in addition to her first Grand Slam at Arthur Ashe Stadium.

Pegula advances to the quarter-final against Spain’s Sara Sorribes Tormo, who defeated Daria Kasatkina 6-4, 1-6, 6-3 to reach her third WTA 1000 quarter-final.

Jil Teichmann advanced to the last eight by defeating 16th-seeded Elena Rybakina 6-3, 6-1. She will face Ukrainian Anhelina Kalinina, who upset reigning U.S. Open champion Emma Raducanu 6-2, 2-6, 6-4 to reach her first WTA 1000 quarter-final. Raducanu said she has been bothered by a back issue.

Meanwhile, Djokovic feels like the hard work is starting to pay off.

Trying to regain his best form after a slow start to the season, Djokovic looked sharp in his opener at the Madrid Open, defeating Gaël Monfils 6-3, 6-2.

“I would probably rate it as the best performance of the year. I felt very good on the court,” the top-ranked Djokovic said after saving all five break points he faced and converting the three he had against the 21st-ranked Frenchman.

It was the Serb’s 18th straight win over Monfils. The match was interrupted at 2-2 in the first set as rain forced the roof on centre court to be closed.

Teenage sensation Carlos Alcaraz kept his good run with a 6-3, 7-5 win over Nikoloz Basilashvili, staying on track for a quarter-final encounter with idol Rafael Nadal. The third-seeded Nadal opens on Wednesday against Miomir Kecmanovic.

Earlier, Rublev reached the third round after rallying to a 2-6, 6-4, 7-5 win over 20-year-old Jack Draper of Britain.

The eighth-ranked Rublev is seeking his first Masters 1000 title. The win in Serbia last month added to his titles in Dubai and Marseille. Only Nadal and Alcaraz have also won three titles this season.

Marin Cilic defeated Albert Ramos-Vinolas 6-3, 3-6, 6-4, while Americans Frances Tiafoe and Jenson Brooksby lost their first-round matches in straight sets. Tiafoe lost to Cristian Garin 6-1, 6-3 and Brooksby lost to Roberto Bautista Agut 6-0, 6-2.

In an all-American match, Sebastian Korda defeated Reilly Opelka 6-3, 7-5.

The Canadian Press, The Associated Press