Milos Raonic became the first Canadian man to reach the Wimbledon semi-finals in 106 years on July 2 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 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.

Watch Wimbledon 2014 Highlights: Rafael Nadal killer Nick Kyrgios beaten by Milos Raonic!