Dundee United needed spot-kicks to dump Ayr United out of the Premier Sports Cup and book their place in the quarter-finals.
The Honest Men took the lead through Tomi Adeloye on 56 minutes before Nicky Clark equalised from the spot with 10 minutes remaining after Jack Baird was sent off.
No 1 Benjamin Siegrist would save twice in the penalty shoot-out at Somerset Park as the Terrors edged out 10-man Ayr and snuck into the hat for the next round.
Drab first half as Utd struggle for foothold
United showed two changes from last weekend’s 1-0 Premiership win over Rangers, with Adrian Sporle and Darren Watson coming in for injured duo Calum Butcher and Logan Chalmers.
New boy Marc McNulty started on the bench as the Terrors began life post-Lawrence Shankland with 900 Arabs watching on in Ayrshire.
Mercurial Argentine Sporle was instantly involved, picking up Clark’s knockdown and firing in an effort Ayr keeper Aidan McAdams collected comfortably.
With Jeando Fuchs a shield in front of the back four, the Tangerines tried to play out from the back and build through the lines.
Liam Smith and Jamie Robson were pushing down the flanks, while diagonals from Ryan Edwards and Charlie Mulgrew were, invariably, finding their target.
However, the home side stood firm and broke well when presented with the opportunity.
On 20 minutes, impressive Rangers loanee James Maxwell seized on a loose ball and careered up the left, firing wide a strike that was always on the rise.
A cross-cum-shot on the half-hour mark from Adeloye got the Somerset Park crowd up as Ayr began to assert themselves.
However, despite what was largely a poor first-half, the Terrors showed some Premiership class in the closing stages.
Quick interchange from Watson, making his first start in tangerine, and Clark had Peter Pawlett bearing down on McAdams’ goal approaching the interval, but the home stopper smothered the chance inside the six-yard box.
Adeloye gives Ayr deserved lead before Clark equalises
The second half started with Ayr in the ascendancy as Siegrist was called into action for the first time.
Michael Hewitt’s deep cross picked out Maxwell on the edge of the box and the instrumental midfield man’s bouncing volley forced Siegrist into an unorthodox claw over the bar.
Andy Murdoch flashed wide from 20 yards on 54 minutes before the pressure told and they took the lead through Adeloye.
Latching on to a long ball, the 25-year-old capitalised on confusion in the United defence between Mulgrew and Robson to poke the ball into an empty net.
Siegrist had initially denied the English striker but he stroked home at the second attempt.
McNulty made his second United debut off the bench on 64 minutes, replacing Sporle as Tam Courts’ men looked for a route back into the game.
However, there was only one team in it as Maxwell, once again a thorn in the visitors’ side, surged forward before scooping his shot over.
Siegrist then had to get strong hands to a Patrick Reading effort from distance.
Shortly after, the buzzing Adeloye rolled Mulgrew before cutting back to McKenzie who saw his effort from 10 yards tipped onto the bar and over for a corner by Swiss stopper Siegrist.
The Tangerines were handed a reprieve with 10 minutes to go as Baird was sent off for bringing down Edwards in the box.
Referee Nick Walsh pointed to the spot and showed Baird a second yellow before Clark stepped up to draw United level from 12 yards, placing the ball beyond the reach of McAdams.
Pushing for the winner, Mulgrew found McNulty in the area with a deep cross but the Reading loanee could only nod over as the game went into extra time.
Clark the spot-kick hero once again
Four minutes into the extra period, United should’ve taken the lead with a training ground free-kick routine.
Mulgrew played in Pawlett down the right who squared for McNulty between the sticks but the 28-year-old stabbed over from eight yards.
Former Ayr man Smith crashed a 25-yard effort off the post moments later before McAdams, at full stretch, denied Clark from close range.
The 10 Honest Men were proving difficult to break down as proceedings headed into the second half of extra time with the game still tied at 1-1.
Both teams huffed and puffed in the final 15 minutes, with Joe Chalmers and Fuchs both going close, but couldn’t make the breakthrough.
In the hat for the QF👊 #DUFCLive pic.twitter.com/X8FqVwxg8r
— Dundee United FC (@dundeeunitedfc) August 14, 2021
Penalties would decide the contest as captain Aaron Muirhead got Ayr off to a scoring start.
McNulty would blast over immediately after, before Siegrist saved from Reading.
Mulgrew found the back of the net to level things up before Sean McGinty, Pawlett, Nick McAllister and Robson exchanged successful spot-kicks.
Siegrist saved from former Dundee hitman Jonathan Afolabi before Clark stepped up to slot the winner beyond McAdams.
Ayr United (4-4-2): McAdams; Houston (Chalmers 111), Baird, Fjortoft, Reading; Hewitt (Miller 111), Muirhead (C), Murdoch (McAllister 103), Maxwell (Salkeld 90); McKenzie (Afolabi 103), Adeloye (McGinty 81).
Subs not used: Albinson (GK), O’Connor and Smith.
Dundee United (4-3-3): Siegrist (GK) (C); Smith, Edwards, Mulgrew, Robson; Pawlett, Fuchs, Harkes (Mochrie 77); Watson (Hoti 88), Clark, Sporle (McNulty 64).
Subs not used: Carson (GK), Newman (GK), Reynolds, Neilson, Freeman and Duffy.
Referee: Nick Walsh.
Attendance: 2,196.