A frustrating afternoon saw St Mirren take a point after a goalless draw with Arbroath at Gayfield Park in the opening match in Group D.
A disappointing afternoon compounded when captain Mark O'Hara received a red card late in the match as Saints ended the game with 10 men before the hosts picked up the bonus point after triumphing 5-3 on penalties.
Mikael Mandron was able to start after being given a 50/50 chance yesterday after a virus. Conor McMenamin, however, would miss out with the virus ruling him out of Tuesday night's pre-season win over Airdrieonians. Goalkeeper Peter Urminsky was given the nod between the sticks and he was called into action early on, making a save at his near post to deny Nikolay Todorov for the visitors.
Roland Idowu had the ball in the net a few minutes later, but the offside flag had already been raised.
Saints were controlling possession and playing most of the game in Arbroath's half, but didn't create anything to trouble Arbroath goalkeeper Aidan McAdams. The best chance of the first 45 came nine minutes before the interval when James Scott should have given Saints the lead. The Arbroath defence couldn't fully clear a Jayden Richardson cross and that saw it fall for Scott, but the forward nodded over from close range.
The restart saw Mandron have a header deflected wide, while Marcus Fraser made a brilliant challenge to block Findlay Marshall a few minutes later.
The manager made three changes before the hour mark with Alex Iacovitti, Oisin Smyth and Jonah Ayunga introduced in place of Richardson, Killian Phillips and Scott as he tried to spark his team into life.
But it was Arbroath who passed up a massive opportunity to take the lead with a little over 10 minutes remaining when Todorov raced on to a ball over the top and beat the offside trap. The forward lifted the ball over the onrushing Urminsky, but put too much on it as it flew over the bar.
Saints saw an appeal for a penalty turned down on 82 minutes when O'Hara went down in the box under a challenge from an Arbroath defender. Rather than point to the spot, referee Steven McLean brandished a yellow card for the Saints captain for what he perceived as simulation.
With five minutes remaining, substitute Evan Mooney was agonisingly close to giving the Buddies a late lead. The 17-year-old just couldn't get his toe on Tanser's low cross with any sort of touch likely to have knocked it beyond McAdams in the Arbroath goal.
Saints' frustration grew when O'Hara received his marching orders on 88 minutes after a foul in the middle of the park saw him pick up a second yellow card.
Mark O'Hara walks off after receiving his second yellow (Image: Willie Vass)
Urminsky made a huge save at the death to take the game to penalties for a bonus point. Calum Gallagher found himself through on goal deep into stoppage time, but Urminsky stood tall to block.
Arbroath were perfect from the spot and when Fraser Taylor saw his spot kick saved by McAdams, that allowed ex-Saint Gallagher to net the final penalty to secure the bonus point for the home side.
Full-Time: Arbroath 0-0 St Mirren (Arbroath win 5-3 on penalties for bonus point)
St Mirren: Urminsky, Fraser, Gogic, Tanser, Richardson (Iacovitti 59), Phillips (Smyth 59), O'Hara (c), John, Scott (Ayunga 59), Mandron (Mooney 74), Idowu (Taylor 74)
Subs Not Used: Mullen, King, Penman, Falconer
Arbroath: McAdams, Watson, Wilkie, Muirhead, O'Brien (c), Cochrane (Pettifer 55), Flynn, Stewart, Marshall, Dow (Reilly 69), Todorov (Gallagher 81)
Subs Not Used: Steele, Gold, Callachan, Pettigrew, Hickey-Fugaccia, Spalding
Referee: Steven McLean
Assistant Referee: Chris Rae
Assistant Referee: Gordon Crawford
Attendance: 1,636 (799 St Mirren supporters)
