A late Gareth Bale double consigned Scotland to a costly defeat in Cardiff, with the task of reaching the 2014 World Cup now appearing an impossible one.
The Scots had led the game until the 81st minute through James Morrison's first half strike, but the Spurs star won and converted a dubious penalty before angling a stunning long range effort beyond Allan McGregor with just minutes remaning.
The defeat leaves Scotland with just two points from their opening three qualification fixtures, moving Wales ahead of Scotland in Group A before Craig Levein's men head to Belgium on Tuesday,
See how the match unfolded below.
