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Dunfermline were the last team to qualify for the last 16 when a late Chris Kane penalty secured St Mirren a win on Sunday that sealed progression as one of the top three runners-up at the expense of Championship rivals Queens Park.
Although St Mirren still top the group on goal difference, defeat means they miss out on Sunday’s draw.
Reacting to the draw at Rangers, manager Craig McLeish said: “I’m disappointed from my point of view that we had a chance to win the group and be one of the top teams and the draw didn’t go our way.
“I thought we conceded a goal, but unfortunately we have ourselves to blame.”
Dunfermline head coach Neil Lennon was a happy man.
“I thought we played well in the last half hour and deserved to win,” he said.
“A home tie is the most important thing, but Ross County have been fantastic this season after a very disappointing retirement, so we won’t take anything for granted.”
Aberdeen, Ayr, Dundee United, Inverness Caledonian Thistle, Kilmarnock, County and Stenhousemuir were the other group winners, with Dundee and Partick Thistle progressing as runners-up.
Celtic, Heart of Midlothian, Hibernian, Motherwell and Rangers were eliminated in the last 16 as they represented Scotland in European competition.
While the Old Firm have drawn against top-flight opposition, the remaining three take on Championship sides, with Hearts hosting Caley Thistle, Hibs at home to Partick Thistle and Motherwell away to Stenhousemuir.
The second round will be played on the weekend of August 15-16.