Scotland 1-0 Netherlands
James McFadden's first half goal gave Scotland a chance of reaching next year's European Championship as the Dutch were beaten at Hampden Park.
The Everton youngster upset the odds in the first leg of the play-off as the Scots defended with determination and rode their luck at times against the nation ranked fifth best in the world.
The visitors hit the woodwork and the Scots made two goal-line clearances as they worked valiantly to protect the lead they will take to Amsterdam on Wednesday.
The Dutch spent most of the second half camped in and around the Scotland penalty area but the home side held firm for a famous win.
Scotland were given a fright inside the first minute when Patrick Kluivert flicked a dangerous low free kick from Andy van der Meyde narrowly wide of the target.
During the brisk opening exchanges, Dutch goalkeeper Edwin van der Sar dealt comfortably with long range efforts from McFadden and Barry Ferguson.
And Gary Naysmith had to make a vital tackle when van der Meyde found space on the edge of the Scotland penalty box.
A neat move involving Darren Fletcher, Ferguson and Dickov opened up the Dutch defence and a flashing cross from the striker forced a corner which led to the opening goal after 20 minutes.
When McFadden's initial delivery came back to him he worked a clever one-two with Fletcher and powered in a shot that flew into the net via a deflection.
The Dutch responded with a close range header from Jaap Stam that Rab Douglas did well to save and a shot from van der Meyde that flew over the crossbar.
Lee Wilkie twice came to Scotland's rescue, making a timely tackle to stop another burst into the penalty area from van der Meyde and then clearing from the goal-line after Douglas had fumbled a cross.
Christian Dailly, who will miss the return leg after picking up a yellow card, blocked a Kluivert strike and Naysmith stopped a header from Frank de Boer on the goal-line as the Dutch pressed forward with menace before the interval.
The second half was just two minutes old when Douglas had to save a header from Ruud van Nistelrooy, following more good work from van der Meyde.
Scotland found themselves pinned back for long spells and were finding it harder to close the Dutch down in midfield.
It was a famous Hampden win for Scotland
A powerful shot from Stam fizzed over the crossbar and Naysmith made another excellent block to deny van der Meyde a clear sight of goal.
With 63 minutes gone van der Meyde saw his shot strike the bar and bounce into the grateful arms of Douglas and substitute Rafael van der Vaart saw his strike gathered by the Celtic keeper soon after.
Dutch replacement Clarence Seedorf was next to see his shot from the edge of the box go close.
With 12 minutes remaining Scotland substitutes Kenny Miller and Stephen Pearson combined to get in behind the Dutch defence but the Motherwell youngster's volley under pressure went narrowly wide.
Ferguson warmed the hands of Van der Sar with a 20 yard shot before Jackie McNamara and Wilkie combined to snuff out Van Nistelrooy in front of goal.
Wilkie was then on hand to clear the danger when Douglas spilled an 86th minute shot from van der Meyde.
Scotland: Douglas, McNamara, Pressley, Wilkie, Naysmith, Fletcher, Dailly, Ferguson, McCann (Pearson 71), Dickov (Miller 66), McFadden (Hutchison 90).
Subs not used: Gould, Graham Alexander, Caldwell, Crawford.
Booked: McFadden, Dailly.
Holland: Van der Sar, Ooijer, Stam, De Boer, Van Bronckhorst (Seedorf 45), Van der Meyde, Cocu,
Davids (Van der Vaart 60), Overmars, Kluivert (Makaay 77), Van Nistelrooy.
Subs not used: Waterreus, Zenden, Reiziger, Van Hooijdonk.
Booked: Ooijer, Stam.
Referee: Terje Hauge (Norway).