Barry Town United's Welsh Cup hopes were dashed in a shock defeat to Caerau Ely on penalties after a 3-3 draw.
Steve Jenkins' men were among the casualties in what was a brutal weekend for Cymru Premier teams entering the fray in the second round.
Five top-flight clubs - including league leaders Penybont - were knocked out, while Barry's Cymru South neighbours Llantwit Major also suffered an early exit on penalties.
Barry were entering the cup on a high after back-to-back league wins saw them break into the top half of the table for the first time this season.
Liam Armstrong replaced goalkeeper Luc Rees, with summer signing Ryan Kavanagh making his first start and both Kayne McLaggon and Josh Yorwerth returning to the XI.
The hosts at Jenner Park went ahead on 34 minutes with a close range finish from Keenan Patten, marking his third goal in as many games.
But barely a minute later, Barry were reduced to ten men when Callum Sainty was shown a straight red for a late challenge on Tom McLean.
The resulting penalty tippled off Armstrong's palm into the top corner of the net as the Cymru South visitors drew level.
Caerau almost went ahead soon after but the Barry keeper was quick to respond to a low drive from seven yards out.
Then on 70 minutes, Ieuan Owen's cross into the box was teed up by McLaggon, who drilled home past former Barry keeper Joe Baker to retake the lead and mark the welcome return to the fold of the club captain, scoring only his second goal this season.
Yet Caerau quickly found another way back when Hywel Davies struck into the bottom corner barely three minutes later to restore parity.
Back came Barry in the 81st minute when Patten rounded Baker before slotting the ball through to Owen, who struck from six yards out into an empty net.
But from a corner four minutes later, Caerau - whose never say die attitude impressed throughout - equalised again through Charlie Lewis to take the game to penalties.
Caerau opened up a 2-0 lead after Patten blasted his effort over the bar while McLaggon's spot kick was denied by Baker.
The decisive moment came when Mclean stepped up for the second time that afternoon to beat Armstrong and record a famous 4-2 victory on spot kicks for the visitors.
Barry, who last won the Welsh Cup in 2003, still have potential silverware to play for this season - as attention turns to Tuesday night's Nathaniel MG Cup quarter final at home to Penybont (7.45pm ko)
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