Raith Rovers 1 Dundee 2
Raith Rovers suffered a last gasp defeat to Dundee in the Betfred Cup tonight after a dramatic ending at Stark's Park.
Lewis Vaughan's superb 89th minute equaliser appeared to have earned Barry Smith's men a penalty shoot-out, and the chance to claim a point, or two, that their performance deserved.
However, there was still enough injury time left for the SPL side to score again to leave Raith with only the consolation of taking positives from defeat for the second match running.
Rovers made one enforced change from the weekend loss at Tannadice as Bobby Barr missed out with a rib injury, and his place on the right wing was taken by 19-year-old youngster Yaw Osei.
There was more youth on the bench with all the subs, Ross Matthews aside, plucked from the development squad. With most of Barry Smith's budget gone, this is sure to be a regular feature of the upcoming campaign.
Rovers competed well in the opening exchanges, and defended strongly from the front, but it took 17 minutes for the game to produce the first effort on goal.
Vaughan slipped Liam Buchanan into space 25 yards out and his low drive took a slight deflection and was comfortably held by Chris Bain.
Rovers then produced the best move of first half as Jason Thomson crossed to Greig Spence, who laid off for Vaughan. The striker's low shot was heading for bottom corner but Bain scrambled to his right to smother the effort.
A Dundee side featuring six new signings were looking rusty in their first competitive game, and Raith threatened again on 34 minutes as Euan Murray's high up and under to the back post was brilliantly brought down by Buchanan, but his volley was straight at Bain.
Sixty seconds later, Dundee's first serious threat came from wide man Randy Wolters who showed great skill to breeze through the Rovers defence before rattling a ferocious shot off the face of the crossbar.
As the half ended goalless, there was more for the hosts to be pleased with than the visitors, and that extended into the second half with Raith continuing to frustrate the visitors, while creating the clearer cut chances, the best of which arrived on 54 minutes.
Great work from Vaughan saw him cut in from left, setting up Buchanan for a clear shot of goal, but the normally deadly striker snatched at his volley, and the ball spun wide.
Dundee introduced Paul McGowan from the bench and the midfielder's first act was to remonstrate with referee Stephen Finnie claiming he was elbowed. He left the field to receive treatment but no action was taken.
Raith again threatened on the hour when a a ricochet sent Spence through on goal but in the act of shooting he was stopped in his tracks by a lunging Kevin Holt tackle from behind.
The striker, who was booked in the first half for diving, claimed a penalty but Finnie signalled that the ball was won. The jeers from the South Stand suggested the home fans who had the clearest view were not convinced.
On 65 minutes a cross into the Raith box was chested down brilliantly by Faissal El Bakhtaoui to Roarie Deacon who flashed a volley narrowly over.
However, Dundee did not start to seriously threaten until the 69th minute introduction of sub striker Sofien Moussa, whose physical presence started unsettling the Raith defence.
His first touch coincided with a clear sight of goal but the Tunisian got the ball caught between his legs and followed with a comical fresh air attempt allowing Lennox to gather.
However, there was no such messing around with his next chance in the 83rd minute, hooking home a volley from close range after the Raith rearguard failed to clear Scott Allan's floated free-kick to give the visitors the lead.
The game looked to be drifting away from Raith but there was a determination about their play as the clock ticked down, which was rewarded with an equaliser in the 89th minute.
Murray, who impressed with a steely display at left back, turned his man to hit the by-line and his cross reached Vaughan around 14 yards out, who swivelled his hips to send a sweet volley inside the near post for a top class finish.
Penalties loomed but Raith could have won it in their next attack as Buchanan drilled a cross into the box that was met by substitute Matthews, but a defender got a half block on his close range effort allowing Bain to make the save.
And in a cruel twist for the home side, Dundee raced up the other end, won a corner, took it short, and Allan crossed for defender Jack Hendry to crash a bullet header past Aaron Lennox to restore Dundee's lead, and win the game.
The defeat leaves Raith without any points from their opening two games against the big spending Dundee clubs, and with more winnable group ties against Buckie Thistle and Cowdenbeath to come, six points may not be enough to retain hopes of qualification.
But for boss Smith, after a start that always looked like being a tough one, the positives will outweigh the negatives.
Raith Rovers: Lennox, Thomson, Murray, Benedictus, Davidson, Callachan, Robertson, Buchanan, Vaughan, Spence (Court 78), Osei (Matthews 66). Not used: Brian, McKay, Berry, Thorsen, Valentine.
Booked: Spence, Court.
Dundee: Bain, Kerr, Holt, O'Dea, Kamara, Allan, O'Hara (McGowan 55), El Bakhtaoui, Deacon, Hendry, Wolters (Moussa 69). Not used: Ferrie, Williams, Spence, Wighton, Waddell.
Booked: Deacon, O'Dea, McGowan.
Referee: Stephen Finnie