Naomi Osaka crashed out of the Libema Open despite fighting to a tie-break in the final set, with Bianca Andreescu progressing to the semi-finals after a 6-4, 3-6, 7-6 (7-3) win.

Osaka's match was interrupted by rain early on with her in the lead, but Andreescu came back out in top form to take the first set.

The Japanese raced through the second though, taking a 5-0 lead before holding off Andreescu's fightback to go into a decider.

Despite an impressive comeback to force a tie-break in the final set, Osaka became sloppy, with her mistakes contributing to the Canadian's path into the semi-final, where she will face Dalma Galfi.

Elsewhere, Alex de Minaur is through to the semi-finals after a comfortable straight-sets victory over Milos Raonic.

Despite a long break due to bad weather, the Australian eased into the next round with a 7-5, 6-2 victory on Friday.

He will face either Ugo Humbert or Gijs Brouwer in the next round.

Data Debrief: Osaka not close enough, De Minaur in cruise control

Despite winning more points (98 compared to 94), and winning more games (16 to 15), Osaka could not hold her nerve in the tie-break to reach the semi-finals.

Competing as the top seed for the first time in his tour-level career, De Minaur felt no pressure as he rallied in the second set to ensure Raonic would not find a way back into the match, winning his last five games in a row on his way to victory.