Aberdeen needed extra-time to edge past lower league minnows Annan Athletic 4-1 in the Premier Sports Cup.
The Reds looked to be heading into the quarter-final draw in regulation time courtesy of a Vicente Besuijen goal.
However Steven Swinglehurst netted late on to force extra-time and ramp up the pressure in a nervous night for the Reds.
Ultimately goals in extra time from Besuijen, Luis Lopes and Leighton Clarkson secured the Dons berth to the last eight.
However it was a tough, tense night though on an artificial pitch against a part-time team second bottom of Scotland’s fourth tier.
The draw for the quarter-finals of the Premier Sports Cup will be made on Wednesday.
It will be shown live on Premier Sports following their coverage of Ross County v Celtic.
Quarter-final ties are due to be played during the midweek of October 18-20.
The summer transfer window closes at midnight on Thursday and Goodwin confirmed he still aims to add ‘at least’ one more signing.
Aberdeen set to miss out on Ronan
Dons gaffer Goodwin has already signed 11 players during an extensive summer rebuild.
However it is understood the Reds are set to miss out on transfer target Connor Ronan with the midfielder expected to remain at Wolves.
Goodwin was keen to be reunited with the 24-year-old who he took to St Mirren on loan whilst manager for the Buddies last season.
Hearts and Hibs were reportedly interested in Ronan who was also linked with German Bundesliga 2 club, St Pauli.
However it is understood Ronan is set to remain at Premier League Wolves for at least the first half of the campaign.
First start for summer signing Morris
Around 1,000 travelling Aberdeen supporters made the 440 mile, nine hour round trip to Annan on Tuesday night
There were three changes to the Aberdeen starting XI that demolished 10 man Livingston 5-0 at the weekend.
Summer signing Shayden Morris came in for his first start since arriving from Fleetwood Town on a four year contract.
Winger Morris, 20, had previously made three substitute appearances Aberdeen.
Winger Matty Kennedy returned to the starting line-up along with Jack MacKenzie who made his first start of the season.
Dropping to the bench were Jonny Hayes and Leighton Clarkson.
On loan Middlesbrough winger Hayden Coulson was not in the squad.
Goal line clearance denies Aberdeen
Underdogs Annan Athletic were the first to forge a clear opportunity in front of goal when Benjamin Luissint burst into the box.
However his low 15 yard shot in the 14th minute flashed wide of the near post.
A goal line clearance denied Aberdeen the opener in the 19th minute.
Matty Kennedy’s drive took a slight deflection that took it beyond keeper Greg Fleming but Steven Swinglehurst cleared off the line.
Aberdeen were struggling to break down a well organised and energetic Annan side content to sit in and then hit on the break.
It was becoming a tougher night than the combination of Aberdeen’s recent positive form and Annan’s lowly league position would have suggested.
Annan Athletic hit the woodwork
The woodwork denied the League Two outfit the opener in the 41st minute when Tommy Muir met a corner swung in by Cameron Williamson.
Muir’s header from the centre of the box cracked off the far post.
Moments later Liam Scales raced onto a Kennedy corner but his glancing header from 15 yards flashed across the face of goal and wide.
Half-time: Annan Athletic 0 Aberdeen 0
Aberdeen boss Jim Goodwin made a double substitution at half-time in a bid to change the tie in the Reds’ favour.
Jonny Hayes was introduced for Kennedy with Luis ‘Duk’ Lopes coming on for Morris.
Winger Hayes made his presence felt immediately when he was at the heart of a strong penalty call.
A shot from Hayes on the left appeared to hit Lewis Hunter’s hand.
However referee Steven McLean waved play on to the dismay of the Dons players calling for spot kick.
Moments later Hayes again threatened when his chipped shot forced keeper Fleming to save at the near post.
Moments later Hayes again threatened when his chipped shot forced keeper Fleming to save at the near post.
Aberdeen break the deadlock
Yet again Hayes was in the heart of the action when his cross found Vicente Besuijen who bundled the ball over the line from close range in the 55th minute.
Keeper Fleming tried to block but the ball passed over the line.
Annan threatened in the 76th minute Muir had a free header eight yards out but keeper Kelle Roos saved.
Lower League Annan levelled in the 81st minute when Swinglehurst outjumped the Dons defence to meet a Chris Johnston corner.
Swinglehurst, the Annan captain, headed in from six yards.
Annan’s tails were up and they pushed forward looking for a late winner.
In the 90th minute, Besuijen shot from the edge of the box but the was straight at keeper Fleming who easily saved.
Early in extra-time Ross McCrorie blazed a right footed shot over from close range.
Aberdeen regained the lead in the 96th minute when Luis ‘Duk’ Lopes met a Leighton Clarkson corner to send in a glancing header.
The Dons fans exploded into celebration – as much through relief as joy.
In the 103rd minute keeper Roos came to the rescue with a vital save to block a low Luissint 12 yard shot.
Dutch winger Besuijen ensured Aberdeen’s place in the quarter-finals when he fired a right footed shot to the bottom right corner in the 105th minute.
It was 4-1 in the 117th minute when Clarkson fired in low from 12 yards.
Full-time (aet): Annan Athletic 1 Aberdeen 4
ABERDEEN (4-2-3-1): Roos 6; MacKenzie 5 (Clarkson 79), Scales 6, Stewart 6, Richardson 6; Ramadani 6, McCrorie 6; Kennedy 5 (Hayes 46), Besuijen 6, Morris 5 (Lopes 46); Miovski 6 (Duncan 79)
Subs: Lewis, Watkins, Polvara, Milne.
ANNAN ATHLETIC (4-5-1): Fleming 6; Williamson 6, Swinglehurst 7, Hooper 6, Kilsby 6; Lowdon 6 (Steele 99), Wallace 6, Hunter 6, Luissint 7, Johnston 6; Muir 7.
Subs: Mitchell, McCartney, Goss, McMenamin.
Referee: Steven McLean
Attendance: 1, 538
Man-of-the-match: Vicente Besuijen (Aberdeen)
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