Shapovalov narrowly defeated Kyle Edmund 7-5, 6-7 (6-8), 6-4 on Friday to become the youngest semi-finalist in the 17-year history of the tournament, reports Efe.
The 19-year-old Shapovalov, a former Wimbledon junior champion who had never won a clay-court match on the ATP World Tour earlier, followed up victories over Tennys Sandgren, Benoit Paire and compatriot Milos Raonic by edging the 22nd-ranked Briton in just under two and a half hours.
Shapovalov had a chance to wrap up the contest in straight sets, but he missed a return of serve on match point in the 12th game of the second set.
Edmund forced a decider by eking out a close tiebreaker, but he was unable to recover after dropping his serve early in the third set.
The 43rd-ranked Canadian showed nerves of steel in the last game, booking his second ATP World Tour Masters 1000 semi-final berth (after the 2017 Canadian Open) with a love service hold.
With the win, Shapovalov ran his career record against the 23-year-old Edmund to 3-2.
Next up on Saturday for Shapovalov will be German world No. 3 Alexander Zverev, who defeated big-serving, ninth-ranked American John Isner 6-4, 7-5.
In the other men's singles semi-final on Saturday, seventh-ranked Thiem face eighth-ranked South African Kevin Anderson.
Thiem had upset Spanish world No. 1 Rafael Nadal 7-5, 6-3 on Friday.
By winning the first set, Thiem also snapped Nadal's record streak of 50 consecutive sets won on clay dating back to the start of last year's French Open.
The Spaniard will drop to No. 2 when the new rankings come out on Monday; Swiss great Roger Federer, who is skipping the clay-court season for the second-straight year, will be back in the top spot for the 309th week of his storied career.
On the other hand, in the women's singles semifinals, Bertens pulled off a surprisingly routine 6-2, 6-2 victory over France's Caroline Garcia at the Madrid Open to book her first-ever berth in a WTA Premier Mandatory final.
Bertens showed no sign of nerves in the semi-final contest, winning the 67-minute encounter without facing a single break point.
She also put constant pressure on the service games of her opponent, who put 81 percent of her first serves in play but managed to win just over half of her total service points.
The world No. 20, who had knocked out two former world No. Dane Caroline Wozniacki and Russian Maria Sharapova earlier this week, will next take on the winner of an all-Czech semi-final pitting Petra Kvitova against Karolina Pliskova.
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