Forfar Athletic came away with a bonus point after a 5-4 penalty win over East Fife in the Betfred Cup with the sides unable to be separated after 90 minutes.
Anton Dowds gave the Fifers the lead early on but John Baird equalised with Chris Kane sent off for a high challenge on Dylan Easton midway through the first half.
Baird’s spot kick was saved by former Loons loanee Brett Long but Marc McCallum denied Ross Davidson and Daryll Meggatt allowing Thomas Reilly to earn the bonus point.
Two changes were made from the midweek defeat to Falkirk with John Kelly and Darren Whyte replaced by Gary Fraser and John Baird.
The first chance of the game fell to Dylan Easton in the fifth minute when he fired straight at Brett Long.
East Fife took the lead sixty seconds later; Kevin Smith saw his shot parried by McCallum, however Anton Dowds was able to force the loose ball over the line despite Jamie Bain’s attempts to clear.
Dale Hilson looked to level things just after the quarter hour mark with a low effort that creeped just past the post while at the other end Scott Agnew curled wide.
In the 27th minute the hosts were reduced to ten men with a chest high challenge on Easton by Chris Kane, giving referee Lloyd Wilson no choice but to show Kane a red card.
The disadvantage wasn’t to deter the Fifers however with Agnew hitting the post five minutes later before McBride saw his header pushed over the bar by McCallum.
Forfar equalised a minute before the break; Hilson’s run into the box ending in his shot deflecting into the path of John Baird to slot home for his first Loons goal.
The second half saw both sides come close to taking the lead with Agnew and Baird being denied by McCallum and Long respectively.
Murray Mackintosh saw his swirling 30 yard effort unorthodoxly saved by Long while Reilly blasted over in the 73rd minute when he was presented with a golden opportunity.
Baird failed to beat Long as the game edged to a close but the final chance fell to Pat Slattery and he could only drag his effort past the post.
Under the rules of the League Cup group stage, any draw after 90 minutes heads to a penalty shoot-out to determine who takes two points from the match, with the loser taking the standard one point for a draw.
The first three penalties were all netted with Craig Watson and Aaron Dunsmore scoring for East Fife while Andy Munro scored for the Loons.
John Baird was first to have his penalty saved and Slattery put East Fife 3-1 ahead. Dale Hilson reduced the deficit with Marc McCallum giving Forfar the chance to level things as he denied Ross Davidson.
Ross Meechan, Anton Dowds and Dylan Easton all converted their spot kicks to take it to sudden death.
East Fife’s Darryl Meggatt stepped up to take their sixth penalty but McCallum pulled off his second shoot-out save, allowing Thomas Reilly to net his penalty and give the Loons the bonus point.
East Fife: Long, Kane, Dunlop, Watson, Smith, Agnew (Thomson 65), McBride (Slattery 65), Dowds, Davidson, Meggatt, Bell (Dunsmore 29)
Subs not used: Court, Watt, Couser
Forfar Athletic: McCallum, Meechan, Bain, Munro, Travis (Kelly 76), Reilly, Fraser (Whyte 67), Mackintosh, Hilson, Easton, Baird
Subs not used: Malone, Coupe, Starkey, Clark, Muir