Blackpool crashed out of the Carabao Cup at the first time of asking with a penalty shootout defeat to League Two side Macclesfield Town.
The Seasiders dominated the first-round tie at Bloomfield Road and had more than enough chances to make it into the next round.
However they were reliant on a last-minute equaliser from Armand Gnanduillet to take the game to spot kicks, which Sol Campbell’s men won 4-2.
During normal time, Pool had taken the lead through a smart Ollie Turton header, only to be pegged back by a Rocky Bushiri own goal.
Macclesfield edged in front in the second period through Virgil Gomis, which appeared to be enough to hand them a smash-and-grab victory.
But while Gnanduillet struck at the death from the penalty spot, it still wasn’t enough for the Seasiders who exited on the penalties.
It means there will be no repeat of last season’s exploits in the competition, which saw them enjoy a money-spinning last-16 tie at Premier League giants Arsenal.
Simon Grayson said he wouldn’t make wholesale changes and he was true to his word, making four in total.
James Husband was an enforced change, the wing back missing out through suspension after picking up a red card in the weekend win at Southend United.
Rocky Bushiri took his place, slotting into the back three, allowing Ollie Turton to move over to left wing-back.
Nick Anderton replaced Curtis Tilt who missed out with a slight knock along with Joe Nuttall, while Christoffer Mafoumbi started in goal in place of Jak Alnwick.
Nathan Delfouneso might have notched his first goals of the season at Roots Hall at the weekend but he dropped down to the bench, giving Ryan Hardie his first start in a Blackpool shirt.
Meanwhile Jamie Devitt and Adi Yussuf were named on the bench to feature for Pool for the first time since signing in the summer.
Pool, brimming with confidence from their opening two victories, started the game brightly, Liam Feeney whipping in a dangerous ball that Macclesfield keeper Owen Evans just about reached ahead of debutant Hardie.
With six minutes on the clock, Armand Gnanduillet wasted a good chance to break the deadlock as he headed over from another threatening Feeney cross.
Grayson’s men dictated the play in the early stages, but chances were few and far between.
Turton showed great determination to beat his man down the left flank before delivering a ball that looked destined to reach Gnanduillet inside the six-yard box, but defender Theo Vassell did well to produce a last-ditch clearance.
The visitors slowly grew into the game and Nick Anderton had to be alert to make an acrobatic clearance to clear Emmanuel Osadebe’s cross.
But Pool responded well, creating a couple of good openings for Hardie in quick succession.
The first came via another dangerous ball into the box from Turton, which found Hardie unmarked only for the striker to flick his header over the bar.
The former Rangers man then dispossessed a Macclesfield defender on the edge of his own box, allowing him to go one-on-one with the keeper only to see his shot charged down by Jay Harris, with the effort deflecting narrowly over the target.
The opening goal finally came with 30 minutes on the clock and it was fitting Pool’s two standout performers who combined.
Feeney whipped in yet another teasing cross and Turton got across his man at the far post to glance a header across the keeper and into the far corner of the net.
The goal put another spring in Blackpool’s step and they went close to adding a second a few moments later, Jordan Thompson firing narrowly over the bar at the back post after Sullay Kaikai had beaten his man with ease down the right.
It seemed just a matter of time until Pool doubled their lead, yet Macclesfield were gifted an equaliser five minutes before the interval following what can only be described as a moment of madness.
Jacob Blyth provided what appeared to be an innocuous cross in from the right that Bushiri should have dealt with without any hassle.
But the on-loan Norwich City man attempted a needless flicked clearance which went horribly wrong, the ball diverting beyond Mafoumbi and into the back of the net.
Kaikai started the second half just where he left off from the first, delighting the crowd with his pace and dynamic runs down the flanks.
Still looking for his first Pool goal, the forward tried to pick out the top corner from 20 yards out but his powerful shot flew narrowly wide.
Pool maintained the pressure and Hardie came agonisingly close to netting on his Pool debut, beating the keeper only to see his low shot cleared off the line by Fiacre Kelleher.
Grayson’s men again came close to edging ahead, Gnanduillet flashing a tantalising ball across the face of the six-yard box which eluded both Hardie and Kaikai by inches.
Pool were awarded a free kick in an inviting position 25 yards out from goal, with Kaikai’s curling effort deflecting just wide.
For all of Pool’s dominance, they somehow found themselves going 2-1 down on 65 minutes, and again it was of their own undoing.
Jay Spearing was dispossessed in his own half, allowing substitute Virgil Gomis the chance to run in behind where he beat Ryan Edwards to the ball before slamming a powerful shot into the back of the net via the underside of the crossbar.
Pool piled on the pressure in response to going behind, Kaikai seeing a close-range shot deflected just wide before Gnanduillet somehow managed to head wide of goal at the back post when it looked easier to score.
The Seasiders were dealt another injury blow with 15 minutes remaining, when skipper Spearing was forced to come after injuring his shoulder after being clattered into by a heavy challenge.
Pool were looking increasingly desperate in their attempts to get back in the game in the dying stages, Edwards bringing a solid stop out of Evans with a powerful volley on the edge of the Macclesfield box.
As the game entered into the first minute of injury time, Blackpool were staring down the barrel of a cup exit at the first time of asking.
But they were handed an invaluable lifeline when Gnanduillet was bundled over in the box, giving the Seasiders a 91st minute penalty.
With Spearing off the pitch, Gnanduillet claimed the match ball to take the penalty and he made no mistake, sending the keeper the wrong way to nestle the ball in the bottom corner.
Both sides almost found time to win it in the final second, Gomis poking just wide of goal for the visitors before sub Harry Pritchard fired over the bar after Michael Nottingham’s cross was parried by the keeper straight to the midfielder.
With no extra time, the game went straight to penalties, and it was Macclesfield keeper Owen Evans who was the hero for the away side.
The shot stopper saved the efforts from Kaikai and Thompson before taking the winning spot kick himself to send Macclesfield through to the second round.
Blackpool: Mafoumbi, Bushiri, Edwards, Anderton, Feeney, Turton (Nottingham), Spearing (Pritchard), Thompson, Kaikai, Hardie (Delfouneso), Gnanduillet
Subs not used: Alnwick, Shaw, Devitt, Yussuf
Macclesfield: Evans, Clarke, Kelleher, Stephens (Gomis), Kirby, Horsfall, Harris, O’Keefe (Archibald), Blyth (Welch-Hayes), Osadebe, Vassell
Subs not used: Charles-Cook, Rose, Cameron, Ironside
Referee: Martin Coy
Attendance: 3,715 (300 Macclesfield)