Milos Raonic defeated wild-card entry Nick Kyrgios of Australia 6-7 (4), 6-2, 6-4, 7-6 (4) Wednesday to become the first Canadian man in more than 100 years to reach the Wimbledon semifinals.
Raonic finished the contest with his 39th ace on his fourth match point, earning a semifinal matchup against seven-time champion Roger Federer.
The 144th-ranked Kyrgios, who upset Rafael Nadal in the fourth round on Tuesday, was attempting to become the first wild card to make the semifinals at a Grand Slam since Goran Ivanisevic at Wimbledon in 2001.
Raonic is the first Canadian men's singles player to reach the semifinals at a Grand Slam since William Johnston at the 1923 U.S. Championships.
The last Canadian man to reach the Wimbledon semis was Robert Powell in 1908.