For the first time in nearly six years, two Canadians will face-off in a semi-final of an ATP Tour event.

Both Félix Auger-Aliassime and Milos Raonic, the two remaining seeded players in Stuttgart, won their quarter-final matches on Friday to set up their second career meeting.

The 18 year old from Montreal started things off by taking down German qualifier Dustin Brown in a tense three-setter 7-6(3), 6-7(2), 7-6(2). All before Raonic defeated Marton Fucsovics 6-4, 6-4 to book his ticket to the semis. Their upcoming match-up will mark the first All-Canadian semi-final on the ATP Tour since the 2013 Rogers Cup (Raonic d. Vasek Pospisil).

Auger-Aliassime has been growing more confident in Stuttgart, and he showed why on Friday.

With the opening set tied 3-3, the Canadian teenager was masterful on serve – knocking three straight aces before Brown failed to return the next one. That was all part of a stretch that saw Félix win 13 of 14 service points. Then, after each player committed a couple of unforced errors and traded mini-breaks, Auger-Aliassime scored the biggest mini-break of the set thanks to a great two-handed backhand return to jump in front 4-2. A lead he wouldn’t look back from.

Later, in the third set, things got a bit testy for the No.7-seed. With the set tied 1-1, Auger-Aliassime saved three break points before eventually holding serve in a game that lasted 10 and a half minutes. The 34 year old German would get it back though. An unforced error in Félix’s next service game put Brown up a break. But the Montrealer was resilient. Down 5-4, he fought off match point before firing a turn-around, cross-body forehand winner to break back and level the match. Then, in the tiebreak, Auger-Aliassime won the first five points and carried that momentum all the way to match point.

Photo: Peter Staples/ATP Tour

Once that match was complete, it was Raonic’s turn to go to work. The 28 year old from Thornhill got off to a strong start, converting on his first break point opportunity in the opening game. From there the Maple Leaf Missile dominated on serve, winning 26 of 33 service points including 88% off his first serve.

In the second set, Milos did more of the same. He tallied his only break point to grab a 4-3 lead. And then, in the final game, the World No.18 notched two of his 12 aces in the match to close it out. Raonic’s latest victory marks the second year in a row that he has made the semi-final in Stuttgart. At last year’s Mercedes Cup, Milos fell in the final to Roger Federer in straight sets 6-4, 7-6(3).

For Auger-Aliassime, he’s headed to his fourth semi-final of the season. In his last tournament, Félix defeated the top-seeded Nikoloz Basilashvili in the Lyon Open semi-finals. He would eventually lose to Benoit Paire, but by reaching the final in Lyon, the 18 year old became the youngest player to reach two or more finals on the ATP Tour since Andy Murray managed the feat at the same age over the 2005 and 2006 seasons.

Now, Félix will attempt to make his third career final when he faces Raonic in Saturday’s semi-final. The two have only previously met once before, with Raonic defeating Auger-Aliassime in straight sets 6-4, 6-4 in last year’s Indian Wells Masters.

Who will win this Clash of Canadians on Saturday in Stuttgart? Will it be Milos or Félix? Tune in on Tennis TV tomorrow around 9:00am ET to watch.

Photo: Peter Staples/ATP Tour