London - Milos Raonic became the first Canadian man to reach the Wimbledon semi-finals in 106 years on Wednesday when he ended the giantkilling run of Australian teenager Nick Kyrgios.
The eighth-seeded Raonic will tackle seven-time champion Roger Federer for a place in Sunday's final after seeing off world number 144 Kyrgios, who beat Rafael Nadal in the fourth round, 6-7 (4/7), 6-2, 6-4, 7-6 (7/4).
Federer had earlier reached the semi-finals for the ninth time with a 3-6, 7-6 (7/5), 6-4, 6-4 victory over compatriot Stan Wawrinka.
Robert Powell in 1908 was the last Canadian man to make the last-four at the All England Club.
Raonic fired 39 aces and 73 winners past Kyrgios. He allowed just 20 points off his own serve and only three in the fourth set.
"It hasn't really sunk it yet. It's great to have this kind of win, especially at a tournament where I always wanted to play so well and haven't in previous years. To turn it around is pretty special," said Raonic.
"It's another step forward. The goal is to be the best player in the world and this is one of those steps you have to take to achieve those goals. To do it on this stage is really special."
Federer enjoys a 4-0 career lead over the Canadian going into the semi-finals.
"I've got to take care of my serve against Roger. It's a great challenge and one I'm gojng to relish," he said.
"I wanted to put myself in this situation so I'm going to compete hard and who knows what can happen."
Wimbledon results on Wednesday, the ninth day of the 2014 championships at the All England Club (x denotes seeded player):
Novak Djokovic (SRB x1) bt Marin Cilic (CRO x26) 6-1, 3-6, 6-7 (4/7), 6-2, 6-2
Grigor Dimitrov (BUL x11) bt Andy Murray (GBR x3) 6-1, 7-6 (7/4), 6-2
Roger Federer (SUI x4) bt Stanislas Wawrinka (SUI x5) 3-6, 7-6 (7/5), 6-4, 6-4
Milos Raonic (CAN x8) bt Nick Kyrgios (AUS) 6-7 (4/7), 6-2, 6-4, 7-6 (7/4)
Eugenie Bouchard (CAN x13) bt Angelique Kerber (GER x9) 6-3, 6-4
Simona Halep (ROM x3) bt Sabine Lisicki (GER x19) 6-4, 6-0