Glentoran crashed out of the County Antrim Shield to East Belfast rivals H&W Welders, losing 4-3 on penalties after the match ended goal-less.
Goalkeeper Michael Dougherty proved the hero in the first round tie at the Oval, saving the final spot-kick taken by Johnny Addis.
Carrick Rangers beat Bangor 4-2 in a shootout after their game ended 1-1.
Goalkeeper Brian Neeson saved from Dominic Melly and Andrew Long and then blasted home the winning penalty.
Joe McNeill had given the Premiership outfit the lead midway through the first half but Richard Gibson replied for last year's beaten finalists just after the hour mark.
Elsewhere, Shield holders Cliftonville progressed to the second round thanks to a hat-trick from striker David McDaid.
The former Coleraine and Derry City forward opened the scoring with a penalty in the 31st minute and added further goals in the 33rd and 60th minutes.
Randal Reid had given the Comrades hope with a 41st-minute strike but the Championship One side were reduced to 10 men soon after when Chris Getty was sent-off.
TJ Murray netted the only goal of the game in the second half as Linfield edged past Newington 1-0 at Windsor Park, while Larne saw off Sport and Leisure Swifts 3-0 at Inver Park with Guillaume Keke (2) and James McCabe on target.
Ballymena United were the night's top-scorers as they put five past near neighbours Glebe Rangers at the Showgrounds to progress to the quarter-final draw.
Paddy McNally, Neal Gawley and Darren Henderson put the Sky Blues in control by the break, with Gary Thompson and David Cushley scoring further goals after half-time.
Meanwhile at Suffolk Road, Crusaders survived a scare against Donegal Celtic, who took the lead through Noel Halfpenny in the 20th minute.
Diarmuid O'Carroll levelled with a penalty on 34 minutes and Barry Molloy nudged his side in front after 69, before O'Carroll missed with a second penalty attempt six minutes from time.
The remaining first round tie between Ards and PSNI will be played on Wednesday night.
Toals County Antrim Shield first round results
BALLYCLARE COMRADES 1 (Reid 41, Getty s/o 42)
CLIFTONVILLE 3 (McDaid pen 31,33, 60)
BALLYMENA UTD 5 (McNally 20, Gawley 27, Henderson 32, Thompson 60, Cushley 62)
GLEBE RANGERS 0
BANGOR 1 (Gibson 62)
CARRICK RANGERS 1 (McNeill 23)
(AET, Carrick Rangers won 4-2 on penalties)
DONEGAL CELTIC 1 (Halfpenny 20, Rosborough s/o 84)
CRUSADERS 2 (O'Carroll pen 34, Molloy 69)
H&W WELDERS 0
(AET, H&W Welders won 4-3 on penalties)
LARNE 3 (Keke 35 & pen 80, McCabe 90)
SPORT & LEISURE SWIFTS 0
LINFIELD 1 (Murray 59)