ESTORIL, Portugal - It took longer than anticipated, but Canada's Milos Raonic is off to a career-first semifinal berth in a clay-court tennis tournament.

The 20-year-old from Thornhill, Ont., defeated veteran Frenchman Gilles Simon, the fourth seed, 7-6 (7-4), 4-6, 6-3 in a quarter-final match at the Estoril Open that took two days to complete due to darkness.

But the fifth-seeded Raonic won't have much time to savour the victory. He was scheduled to play his semifinal match later Saturday but at least it will be against a familiar foe -- Spaniard Fernando Verdasco.

This will mark the third meeting between the two players this season. The second-seeded Verdasco also needed two days to down South African Kevin Anderson 6-7 (2-7), 6-2, 6-3 in a contest which finished in rain.

Raonic beat Verdasco in their two previous meetings. Raonic earned his first career ATP title at the Spaniard's expense in San Jose in February, then defeated him the following week in an opening-round match in Memphis, Tenn.

Raonic had seven aces and five service breaks against Simon in a match that lasted a combined two hours 31 minutes.

On Saturday, Raonic captured the incomplete first set in a tiebreaker before Simon rallied to win the second.

Raonic stormed out to a 4-2 lead in the fourth but couldn't close it out as Simon saved two match points. But Raonic finally advanced on his third opportunity.