Milos Raonic became the first Canadian man to reach the Wimbledon semi-finals in 106 years on Wednesday when he ended the giant-killing 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 a 6-7 (4-7) 6-2 6-4 7-6 (7-4) victory over world No.144 Kyrgios, who beat Rafael Nadal in the fourth round.

Federer had earlier reached the semi-finals for the ninth time with a 3-6 7-6 (7-5) 6-4 6-4 win 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 going 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?”