It was a case of unlucky number 13 for Andy Murray as he crashed out of the ABN AMRO World Tennis Tournament in Rotterdam in a straight sets defeat by Gilles Simon.
Murray had won his last 12 matches against Simon but looked off-colour against the Frenchman on Friday 13th as his opponent came through to win 6-4 6-2.
Simon will now face Tomas Berdych in the semi-finals.
The match started in the worst possible way for Murray as Simon broke his first service game then moved into a 2-0 lead to pile the early pressure on the Scot.
Murray held his next serve but Simon took his own service game then broke the top seed again to ease 4-1 ahead.
The Frenchman then powered 5-1 in front on his own serve leaving Murray with a mountain to climb in the first set.
The number one seed did not falter with the ball in hand on his next serve to pull back to 5-2 then broke Simon to cut the gap to two games.
Murray held again thanks to a Simon error to trail 5-4 then pushed his opponent all the way as he served for the set, but the Frenchman came through to take it 6-4.
Simon started the second set in exactly the same way as the first - with a break of the Murray serve - before following it up with a hold and another break to move 3-0 clear.
Another hold meant Simon had total control of the set but Murray finally got a foothold at 4-1 after clinging on to his service game.
A double fault by Simon in the next handed Murray two break points, and the beaten Australian Open finalist took the first opportunity to cut the gap to 4-2.
However, Simon broke right back after Murray floated a chip into the net, giving him the chance to serve for the match.
The world number 19 did just that, with an out-of-sorts Murray flashing a forehand wide to gift Simon two match points.
Murray pulled it back to deuce but Simon came through to take the second set 6-2 and wrap up a crushing defeat.
Earlier, Berdych had booked his place in the last four thanks to a 6-1 6-4 victory over Gael Monfils.