Institute pulled off a remarkable 4-3 triumph after extra time at Seaview to end Crusaders' 12-match unbeaten run in the most striking result of a night of upsets in the League Cup.
The Championship One side triumphed thanks to goals from Dean Curry, a Garbhan Friel penalty, an own goal by Crues keeper Graeme McKibben and an extra-time Gareth Brown winner. It was a deserved victory by Kevin Deery's men, who currently sit third from bottom in the second tier. The Crues goals came courtesy of ex Stute striker Stephen O'Flynn and two Andrew Mitchell penalties.
Elsewhere, new Linfield boss David Healy oversaw his new side crash to a 0-1 defeat at the hands of Ballinamallard United, thanks to a 70th minute Jonny Lafferty strike, while an early Shea Conaty strike for Portadown wasn't enough as a David Miskelly own goal and Stephen Murray penalty was enough for a Warrenpoint victory at Shamrock Park.
Holders Cliftonville progressed past Dungannon Swifts 4-3 on penalties after a thrilling 3-3 draw, which saw the Swifts' Paul McElroy score a remarkable strike from his own half. Coleraine also needed penalties to see off Championship One leaders HW Welders. The Welders had led through a Ryan Deans shot but James McLaughlin's ninth goal of the season brought the Premiership side level and they progressed 3-1 on spot-kicks.
A Stephen Gordon double and late Curtis Allen strike ensured Glentoran knocked out Carrick Rangers, who had scored early on through Brian McCaul, a Jonny Taylor header saw Ballymena edge past Limavady and Ards won 2-0 away to Annagh United thanks to a Ross Arthurs header and Gary Warwick strike.
Annagh United 0-2 Ards
Coleraine 1-1 HW Welders (3-1 on penalties)
Crusaders 3-4 Institute (AET)
Dungannon Swifts 3-3 Cliftonville (3-4 on penalties)
Glentoran 3-1 Carrick Rangers
Limavady United 0-1 Ballymena United
Linfield 0-1 Ballinamallard
Portadown 1-2 Warrenpoint Town