Airdrie lost out 5-4 on penalties to Annan Athletic after a last-gasp equaliser in injury time.
It was a story of redemption for youngster Matthew McDonald on his Airdrie debut in the Premier Sports Cup.
The 18-year-old was introduced just before half-time but he conceded a penalty on 67 minutes for a naive challenge.
However the former Motherwell academy star displayed great strength of character to equalise with virtually the last kick of the game to take the game to penalties.
Calum Gallagher missed for Airdrie which allowed Wallace to give Annan a 5-4 win on penalties.
Airdrie boss Ian Murray named a strong starting line-up with only three players from last season - Max Currie, Callum Fordyce and Gallagher - in the starting eleven.
Annan's side featured a host of familiar names including former Clyde winger Chris Johnston as Peter Murphy aimed to start the season with a positive result.
The Diamonds started brightly and they threatened down the left wing through Rico Quitongo but an Annan defender blocked his cross.
From the resulting corner, Dylan Easton's dangerous in-swinging cross narrowly evaded the head of Callum Fordyce and the ball bounced to safety.
Gallagher was Airdrie's star man towards the end of last season as he embarked on a rich vein of goalscoring form.
The 26-year-old linked well with striker partner Jordan Allan on 11 minutes but his ambitious effort from range flew over the bar.
Annan settled impressively into the game and after Airdrie's dominant start, the visitors enjoyed a good spell of possession and territory.
Dylan Easton was the catalyst behind Airdrie's improved second-half performance in the NL Cup final defeat last weekend and the 27-year-old was the host's most threatening player in the first half.
The former Kelty Hearts star played a gorgeous pass through to Quitongo on 27 minutes before he weaved past a couple of challenges in the box but his shot was blocked on the half hour.
Airdrie improved as half-time approached and Gallagher forced Ryan Adamson into a smart save from his powerful effort on 38 minutes.
Moments later, Sam Wardrop couldn't get a proper connection on the ball after Scott Agnew's deflected free-kick fell to him just eight yards out.
Diamonds boss Murray was forced into a change just before the break when Easton limped off to be replaced by former Motherwell youngster Matthew McDonald.
Airdrie goalkeeper Currie bailed his side out on 54 minutes when he made an excellent point blank saved to keep out Dominic Docherty's header from just six yards out.
Docherty came close again on 58 minutes minute when he fired over the bar after a brilliant run from Aidan Smith.
Murray introduced new signing Salim Kouider-Aissa on the hour mark in search of a winner.
But it was Annan that grabbed the initiative and they went ahead on 67 minutes courtesy of Tony Wallace's penalty.
Substitute McDonald showed his inexperience as he fouled Smith who anticipated the contact and Wallace stepped up confidently to fire high past Currie.
Airdrie threw men forward in the closing stages and captain Fordyce bulleted a header wide on 81 minutes but they deservedly equalised right at the death through McDonald.
Airdrie: Currie, Wardrop, Watson, Lyons, Fordyce, Quitongo, McCabe, Agnew, Easton(McDonald, 44'), Gallagher, Allan ( Kouider-Aissa, 60')
Subs: Cantley, Kerr, Ritchie.
Annan: Adamson, Barnes, Birch, Moxon, Douglas, Swinglehurst, Wallace, Docherty(Hunter, 81) Smith, Fleming, Johnston ( Anderson 64')
Subs: Fleming, Lowdon, Steele.
Goal: Wallace 67'
Booked: Moxon, Swinglehurst
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