Livingston's bid to reach the knock-out stages of the Premier Sports Cup suffered a major blow after the 10-men hosts missed a late penalty as they fell to a 2-1 home loss to Championship side Inverness Caledonian Thistle.
The Lions could feel somewhat unlucky to have been a goal down at the break after Austin Samuels tapped home at the back post seven minutes before the interval.
But the turning point came just before the hour mark when keeper Max Stryjek raced from his goal and clattered into the Thistle scorer and was promptly shown red.
Livi were rattled by that and were quickly further behind when the energetic Daniel MacKay blitzed beyond his marker and fired into the far corner midway through the second half via a deflection from the unfortunate James Penrice.
To their credit, they did at least show plenty of fight and it was game on six minutes from time as Jason Holt wonderfully turned his marker on the edge of the box before caressing the ball beyond Mark Ridgers.
And they had the perfect opportunity to dramatically take the tie to penalties three minutes later when referee Alan Muir pointed to the spot - only for Holt to fluff his lines and sky harmlessly over the crossbar.
The hosts started the brighter of the two side and showed the greater attacking threat from the off. Dylan Bahamboula was inches away from connecting on a Nicky Devlin cross before Esmael Goncalves saw his point-blank effort saved by Ridgers after Joel Nouble had waltzed his way inside the box under pressure before teeing up the striker.
Having failed to threaten, Inverness almost took the lead against the run of play on 20 minutes when a Robbie Deas header from a free-kick was tipped onto the bar by Stryjek. The Polish stopper would be called into action again seven minutes later when he palmed away a MacKay curling effort after the on loan Hibs man had sprinted beyond Jack Fitzwater.
A two-minute spell just before the break saw Livi inches away from scoring what surely would have been goal of the season - only to then promptly fall behind.
After intercepting a quickly taken free-kick, Devlin spotted Ridgers off his line and tried an audacious effort from five yards inside his own half. The scrambling keeper was able to get back in time enough to dive back and tip the ball onto the bar.
Almost instantly, the Championship visitors were in front as a Thistle counter-attack left the home side's defence outnumbered with Samuels on hand to fire home at the back post on 37 minutes after MacKay rolled the ball across goal.
Martindale introduced Bruce Anderson at the break in a bid to get back into the contest but the hosts would dig themselves into an even deeper hole just before the hour mark as they were reduced to 10 men.
A long ball over the top led to a miscommunication in the Livi back-line with Stryjek racing out of his goal and clattering into Samuels and promptly being shown a red card.
Back-up Ivan Konovalov didn't have to wait long to be called into action as he tipped the resulting free-kick from Cameron Harper over the bar.
The Russian was helpless minutes later, however, when the impressive MacKay waltzed his way beyond Pittman wide on the left and fired home Caley's second across goal and into the far corner.
It appeared to be game firmly over at that point but the hosts fought back when Holt curled home from the edge of the box. And the former Hearts man had the chance to rescue the tie three minutes later when George Oakley was adjudged to have dragged down Scott Bitsindou inside the box but he would blaze his effort over the bar and leave the Lions' hopes of a last-16 place in doubt.
Livingston: Stryjek; Devlin, Cancar, Fitzwater, Penrice; Kelly (Bitsindou 74), Holt, Pittman; Nouble (Shinnie 74), Goncalves (Anderson 46), Bahamboula (Konovalov 61). Subs not used: Longridge, Montano, Brandon, Mullin, Omeonga.
Goal: Holt (84).
Red card: Stryjek (58).
Missed penalty: Holt (87).
Inverness CT: Ridgers; Carson, Delaney, Deas, Harper; Allardice (Oakley 77), MacGregor, Hyde (Boyd 63), D. MacKay (Doran 71); Shaw (McKay 63), Samuels. Subs not used: C. MacKay, Cairns.
Goals: Samuels (37), MacKay (67).
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