Livi saw their hopes of reaching the knockout stages of the Betfred Cup all but ended as Ayr United left with all three points on a disappointing night at the Tony Macaroni Arena.
The Lions knew three points were essential to keep their chances of advancing from Group F alive but a below-par performance allowed Ayr to claim their fourth successive win in West Lothian and go top of Group G.
Livi boss David Hopkin made two changes to his side from the 3-0 win over Edinburgh City in their last competitive outing, one of them enforced as Liam Buchanan replaced the injured Nicky Cadden, though the ex-Airdrie man was fit enough to be named on the bench. Jordan Sinclair came in for Shaun Byrne.
The match got underway in torrential rain and it was Livi who started the brighter, creating the first half chance on seven minutes when Buchanan battled well to win possession in midfield before firing an ambitious effort over the bar from 35 yards. The Lions frontman came within inches of breaking the deadlock a minute later when he picked up Jackson Longridge’s throw-in and unleashed a fine volley which clipped the bar on its way over.
Livi went close again on 12 minutes when, after Daryll Meggatt was booked for hauling him down, Danny Mullen met Sinclair’s free kick with a glancing header that Greg Fleming did well to save. Buchanan and Mullen then combined well to release Josh Mullin but his square ball was fractionally overhit and Dale Carrick was unable to beat Fleming from a tight angle.
Having dominated the opening stages, Livi were hit with a sucker punch on 19 minutes when a counter attack from the visitors ended with Peter Murphy firing an unstoppable effort into the top corner from 25 yards. Livi responded well and a Mullin free kick caused chaos in the visitors box before the ball was launched clear. Ayr came close to a second on 27 minutes when Nicky Devlin was played in on the overlap and he fired in a powerful effort which Liam Kelly saved well.
Livi continued to do most of the pressing and came close to an equaliser on 29 minutes when Mullen latched onto Buchanan’s pass but fired just wide from the edge of the box. The final chance of the half saw Sinclair fire over the edge of the box after a succession of long throws as Ayr went in at the interval in front.
Half-time: Livingston 0-1 Ayr United
Livi made one change at the break as Dale Carrick, who suffered a broken hand during the first half, was replaced by Cadden. The Lions continued to press as the second half got underway and Murphy had to stretch to head away a terrific cross from Mullin. Murphy was replaced shortly after as Craig McGuffie came on in his place.
Another cross from Mullin was cleared to the edge of the box where Cadden gathered but he could only send his shot wide. Ayr midfielder Ross Docherty was fortunate to escape with just a yellow card on 56 minutes after a ferocious lunge through the back of Sinclair, who was replaced by Byrne shortly after.
Ayr came close to a second on 62 minutes when the ball fell to Paddy Boyle at the edge of the box and he fired in a fine angled drive that seemed destined for the top corner, only for Kelly to produce a magnificent fingertip save to divert it onto the bar. Longridge picked up a yellow card for a foul on Robbie Crawford before trying his luck from 30 yards with an effort that flew over the bar.
Ayr made their second change on 71 minutes as Mick Wardrope replaced Docherty, who was perhaps onto his last warning, before Livi came agonisingly close to an equaliser when a great run from Byrne saw him create a chance for Cadden but his shot rolled narrowly wide.
Matthew Knox came on for Mullen as Livi made their final change but it had little time to take effect before the visitors doubled their lead when McGuffie slotted past Kelly from close range. The Livi players appealed furiously for offside but their cries fell on deaf ears.
Livi almost pulled one back on 85 minutes when Cadden curled a free kick straight at Fleming before Crighton fired a 30 yard effort well wide in the final minute. Ayr held out comfortably, though, to make it three wins out of four in the Betfred Cup and put themselves on the brink of qualification.
Livingston: Kelly, Miller, Lithgow, Longridge, Halkett, Sinclair (Byrne 66), Crighton, Mullin, Mullen (Knox 75), Carrick (Cadden 45), Buchanan
Subs not used: Jamieson, Pittman, Orr, Watt
Ayr Utd: Fleming, Devlin, Boyle, Murphy (McGuffie 50), Crawford, Donald, Adams, Docherty (Wardrope 70), Cairney, Meggatt, Thomas (O’Connell 75)
Subs not used: Hart, McCracken, Rose
Goals: Murphy (19), McGuffie (78)
Referee: David Lowe
Match report: Andy Crawford