Canada’s Milos Raonic upset world number two Roger Federer 7-6 (7-5) 7-5 to reach the Paris Masters semi-finals on Friday, keeping alive his bid to reach the World Tour Finals.

It was the first victory for the big serving right hander over Federer in seven meetings and sets up a last-four matchup against Tomas Berdych.

Raonic needs to win the tournament to guarantee his place in the season-ending finale in London while Federer suffered a blow in his bid to overtake Novak Djokovic in the race for the season-ending world number one spot.

Berdych guaranteed his place in the London field for the fifth straight year on Friday as he

defeated South African Kevin Anderson 6-7 (4-7) 6-4 6-4 in just under three hours.

Djokovic is next on court against Andy Murray with fourth seed David Ferrer taking on Japanese star Kei Nishikori in the concluding quarter-final.