Scotland’s World Cup qualification hopes are in tatters after suffering a crushing 2-1 defeat to Wales in Cardiff.
The Scots, searching for their first victory on the road to Brazil, had taken the lead through James Morrison in the first half, but a penalty and a stunning long range strike from Gareth Bale gave Chris Coleman’s side the win, moving Wales ahead of Scotland in Group A.
The defeat leaves Scotland with just two points from their opening three qualification fixtures, making the target of reaching the World Cup in two years time seem an impossible one.
Manager Craig Levein will undoubtedly face more questions over the security of his position as Scotland boss as they now head to Belgium to face the group leaders on Tuesday night.
Steven Fletcher returned from international exile to lead the line for the Scots at the Cardiff City Stadium, with Darren Fletcher also returning from a lengthy absence to captain the Scots.
Kris Commons also made the starting lineup having been called up during the week following an injury to Robert Snodgrass, alongside Scott Brown, who missed the last international double-header with an ongoing hip problem.
Wales were led by new captain Ashley Williams, who took over the armband from Aaron Ramsey, as the home side made four changes from the 6-1 drubbing in Serbia.
In place of injured goalkeeper Boaz Myhill and defender Adam Matthews, Lewis Price and debutant Ben Davies came into the team, along with midfield pair David Vaughan and Joe Ledley.
Scotland looked the more composed side in the very early exchanges, but Wales soon found some rhythm and Bale sent a dipping effort off-target from distance in the seventh minute.
The Tottenham man tried his luck again three minutes later, latching on to Chris Gunter's lofted ball down the right channel, cutting in and bending a shot across Allan McGregor that went just wide.
The best Scotland could muster in response was an Alan Hutton effort that went over, before Ramsey teed up Joe Allen for a strike that Gary Caldwell managed to bock.
Steve Morison then passed up a great chance to break the deadlock when he nodded wide from a lovely Bale cross from the right and it was an opportunity they would be left to rue as Scotland surged into the lead seconds later.
Goalkeeper Allan McGregor punted a long ball up the pitch, which was met by Steven Fletcher who flicked on for Morrison to drive home with a cool finish with 27 minutes on the clock.
Steven Fletcher could have added his own name to the scoresheet but connected awkwardly with an inviting cross from Fox and the chance was lost.
Bale was causing plenty of problems with his pace and delivery and another impressive cross found Ramsey but he blasted over with half time approaching.
Scotland also passed up a decent chance just before the break when Steven Fletcher again nodded down for Morrison but, this time, he volleyed over.
Levein made a change at the break with Brown, clearly still troubled by his injury, replaced by Charlie Adam.
Wales tried to haul themselves back into the game in the second half and claimed for a penalty when Ramsey went to ground under pressure from Adam but there was no spot kick from the German referee.
Morrison had another chance to leave the net bulging with a point-blank effort that stung the palms of the Wales goalkeeper.
Ramsey should have levelled for the home side when he burst through on goal with only McGregor to beat but the goalkeeper raced off his line to block with his legs.
The Scots thought they had doubled their lead when Steven Fletcher bulleted a header into the back of the net with 15 minutes remaining.
But the assistant referee deemed Adam's cross had swerved out of play and the effort was disallowed, although television pictures suggested this may not have been the case.
Wales were back on level terms with 10 minutes to go when Maloney was deemed to have fouled Bale in the box, who got up and rifled past McGregor from the penalty spot.
Hutton then fired just over as the Scots searched for a late winner but the honours went to Wales instead with a minute to go when Bale curled a stunning left-foot shot past McGregor to claim a last-gasp win and leave the Scots deflated.
WALES: Price, Gunter, Davies, Vaughan, Blake, Williams, Allen, Ledley (Robson Kanu), Morison (Davies), Ramsey, Bale. Subs: Brown, Ricketts, King, Richards, Church, Vokes, Wilson, Fon Williams.
SCOTLAND: McGregor, Fox, Berra, Caldwell, Hutton, D.Fletcher, Brown (Adam), Morrison (Mackie), Maloney, Commons (Miller), S.Fletcher. Subs: Mulgrew, Gilks, McArthur, Martin, Phillips, Webster, Marshall, Forrest.