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Andy Geggan marked his return to Ayr with a derby winner to leave Kilmarnock in danger of a second consecutive group-stage exit from the Betfred Cup.
The defender capitalised on poor marking to head the only goal at Somerset Park 39 minutes into his first game since returning from a five-year spell at Dunfermline.
The goal was thoroughly deserved and Ian McCall's side showed resilience to extend Kilmarnock's 24-year run without victory at their Ayrshire rivals' ground, which hosted a near capacity crowd of about 6,000 fans.
Kilmarnock announced the signing of Alex Samizadeh from Bolton before kick-off and the teenage striker started on the bench as Stephen O'Donnell, Calum Waters, Kirk Broadfoot and Alan Power made their debuts.
Ayr, who went full-time following relegation from the Championship, created the first real opportunity as Jamie Adams was allowed a free header on the six-yard line following a corner but Jamie MacDonald got down well to stop.
Power had a half-chance after a late sprint into the box to meet a corner but he volleyed well over and soon gifted possession away inside his own half before MacDonald pushed Craig Moore's shot away.
The goalkeeper then parried Declan McDaid's free-kick wide of his near post but was left exposed again from the resulting corner as Geggan met McDaid's delivery to nod home from close range under little pressure.
Jordan Jones had looked the most threatening visiting player and Ayr often resorted to foul means to stop the winger's forward runs.
However, referee John Beaton ruled there was no infringement when he went down inside the box after wriggling between two opponents early in the second half.
Jordan Hart was finally forced into action following Rory McKenzie's well-hit long-range drive but the home goalkeeper proved up to the task as he gripped the ball on the soaked surface.
Kilmarnock were enjoying plenty of possession but Ayr defended their box well and MacDonald was called into action several times as Ayr put their rare second-half attacks to good effect.
Jones forced Hart into a decent stop after cutting inside before MacDonald prevented Robbie Crawford netting a sensational second after a mazy run, but one goal proved enough.
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KIL
