Darren Fletcher will not be captaining the Scots at the World Cup finals
Scotland's World Cup dream ended as a late Eljero Elia goal gave Group Nine winners Netherlands victory despite a brave effort from George Burley's side.
Dirk Kuyt struck the Scots' post early on, while Kenny Miller fired against the Dutch crossbar.
A Steven Naismith shot struck a Dutch post and Miller's effort on the rebound was saved by Michel Vorm.
But the Dutch made it eight wins out of eight when Elia pounced on David Weir's mistake to run clear and score.
And so the dream died with nine minutes left on the ninth day of the ninth month of 2009.
It had been a terrific performance by the Scots, but Elia's strike meant that Norway clinched the runners-up spot after their 2-1 victory over Macedonia - and raises question marks about the future of manager Burley.
Both sides had been forced to do without their first-choice goalkeepers, Scotland's Craig Gordon and Holland's Maarten Stekelenburg failing fitness tests earlier in the day.
David Marshall came into the home side after losing 11 goals in his previous three internationals and nearly conceded another within minutes of the kick-off.
Interviews - George Burley, Darren Fletcher and David Weir
Kuyt fired a snap shot from 20 yards that struck the outside of the far post before the ball bounced clear.
Scotland soaked up that early pressure and ought to have opened the scoring after nine minutes.
Alan Hutton's superb early cross found Scott Brown sneaking unmarked into the box, but the midfielder skewed his half-volley just wide from eight yards.
Wesley Sneijder had recovered from an injury picked up against Japan to start for the Dutch and forced Marshall into his first save after 24 minutes with a 22-yard drive that the keeper did well to turn over the crossbar.
That sparked the visitors into life and Scotland were split open by a fine through ball from Robin van Persie, but Marshall did superbly to block Arjen Robben's low effort from 14 yards.
The home side responded and Miller fired a volley off the underside of the crossbar from a difficult angle wide on the right.
Naismith, playing wide on the right in his first Scotland start, had the ball in the net off the far post but was pulled up for offside - a narrow but probably correct decision.
The Rangers forward struck the post with his next effort after 38 minutes, his low drive being turned on to the post by Vorm and Miller should have found the net from eight yards only for the goalkeeper to recover and turn the ball to safety.
Elja (centre) scored the winner for the Dutch late in the game
Scotland were under pressure at the start of the second half and the Dutch went close twice.
Kuyt headed over from a good position following a corner then Marshall somehow managed to block the ball with his body after Robben had turned Hutton inside the box before letting fly from 10 yards.
Burley, who had made five changes to his side for the match, withdrew holding midfielder Paul Hartley and brought on winger Kris Commons and pushed Naismith forward as he went all out for the win the Scots so desperately needed.
It almost paid off immediately, with Miller being unlucky not to break the deadlock after 69 minutes when his snap shot struck the fortunate Vorm and spun clear of the goalkeeper's far post.
Scotland's hopes were dashed when Weir was caught flat-footed by a long clearance out of the Dutch defence and the centre-back's poor header was pounced on by Elia, who coolly rounded Marshall to score.
Substitute Garry O'Connor went close with a first-time attempt to lob Vorm, but yet another Scottish qualification campaign ended in disappointment as the Dutch became the first side in 28 years to finish the qualification campaign with a 100% record.
Scotland: Marshall, Hutton, Weir, McManus, Whittaker, Hartley (Commons 67), Naismith, Brown, Darren Fletcher, Maloney (O'Connor 83), Miller. Subs Not Used: Neil Alexander, Graham Alexander, Gary Caldwell, Steven Fletcher, Rae.
Booked: Naismith, Hartley, Darren Fletcher.
Netherlands: Vorm, Van Der Wiel, Ooijer, Mathijsen, Van Bronckhorst, Sneijder (Van der Vaart 77), De Zeeuw, De Jong, Robben (Elia 73), van Persie (Huntelaar 84), Kuyt. Subs Not Used: Velthuizen, Heitinga, Schaars, Braafheid.
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