St Johnstone had to fight back from behind twice to claim a draw with Queen of the South in the Premier Sports Cup – then lost a second consecutive shoot-out.
The Perth side now sit on just two points, two games into the group stages, with two left to play (Elgin City away and Ayr United at home).
Anything less than six points from those fixtures is likely to see Saints crash out, with only group winners and the best three runners up securing qualification.
The Perth side, wearing their new teal and magenta away kit, fell behind to their League One opponents just 12 minutes in when a Lee Connolly header from just outside the six yard box beat Elliot Parish.
Jamie Murphy (a 10th minute replacement for the injured Ali Crawford) and Graham Carey both saw efforts blocked before the break as Callum Davidson’s side toiled to find a way back into the game.
But Queens came closest to adding to their lead before the break, with Connolly and Ruari Paton seeing shots on goal saved by Parish.
Charlie Gilmour – again given a start at right wing back for the Perth side – was replaced by Michael O’Halloran at half-time as Saints gaffer Davidson sought to inject some pace.
Four minutes after the break, the equaliser arrived courtesy of Murphy, who worked his way into the box before firing a left-footed shot into the far corner of the net.
Saints enjoyed a brief flurry of chances after the equaliser, but could not find a way to goal.
And they were made to pay when Queens re-took the lead with 25 minutes to go, Paton firing home, assisted by Ciaran McKenna, after the St Johnstone defence failed to deal with a corner.
Callum Davidson threw on Theo Bair and Max Kucheriavyi for Graham Carey and Stevie May, but Queens continued to threaten, with Connolly missing one shot narrowly to the right, before Parish saved a second.
However, with six minutes to go, Murphy pounced again, firing home from inside the box, assisted by Bair, to level the scores.
Having lost 5-4 on penalties after being held 0-0 by League Two Annan Athletic, Murray Davidson and Kucheriavyi both saw spot kicks saved to ensure the bonus point again slipped through Saints’ grasp.
St Johnstone: Parish, Gilmour (O’Halloran 46), Brown, Mahon, Considine, Montgomery, Hallberg, Davidson, Carey (Bair 68), Crawford (Murphy 10), May (Kucheriavyi 69).
Unused subs: Sinclair, Ballantyne, Ferguson, Steven.
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