Preston North End suffered injury-time heartache as Coventry City knocked them out of the Johnstone’s Paint Trophy at the Richo Arena.
Graham Westley’s men led 2-1 through goals from Luke Foster and Stuart Beavon going into stoppage-time.
But Carl Baker drove in a 92nd minute equaliser, before former PNE loanee Leon Clarke hit the Sky Blues’ winner 90 second later.
It was a cruel end to an exciting game, North End looking on course for a place in the northern area final until the late turn around.
Steven Jennings had given Coventry the lead four minutes before the interval, Foster levelling matters with his first goal for PNE in the 67th minute.
Beavon’s shot deflected off home centre-half Richhard Wood to give the visitors an 80th minute advantage.
Then disaster struck in the five minutes of time added on, leaving North End’s 485 travelling fans in despair.
Graham Westley had made four changes to the North End side.
New signing Joe Garner was handed his PNE debut up front, with Joel Byrom, Lee Holmes and Foster returning to the starting XI.
It was Holmes’ first appearance since suffering a groin strain in the league fixture against the Sky Blues before Christmas.
North End lined-up with a diamond-shape midfield, John Welsh in the holding role with Nicky Wroe and Byrom in front of him, Holmes at the forward point of it behind strikers Garner and Beavon.
A lively opening saw both sides on the attack as they looked to gain an early foot hold in proceedings.
A ball over the top of the PNE defence put Clarke clear in the box, the striker’s attempted lob not having the height to clear Steve Simonsen who saved easily.
Gary McSheffrey then cut inside from the left-wing and let fly with a shot from 20 yards which flashed inches past the post.
Shane Cansdell-Sherriff was an early casualty of the busy early exchanges, limping off with an injury in the 18th minute and replaced by Chris Robertson.
North End appealed for a penalty when Sky Blues right-back Jordan Clarke appeared to handle in the box but referee Robert Madley was unimpressed.
Mr Madley was just as unimpressed with Garner leading with his arm as he challenged for a high ball, the debutant earning the night’s first yellow card.
Good build-up play involving Beavon and Holmes presented Wroe with a shooting opportunity on the edge of the box, but the midfielder lifted his left-foot effort too high.
There was a let-off for the visitors in the 37th minute when McSheffrey’s defence-splitting pass put Clarke in the clear on the left side of penalty area.
He shot low across Simonsen, the ball travelling a yard wide of the back post when really he should have hit the target.
PNE responded by going close themselves, Garner firing into the side netting from a tight angle after Holmes’ quickly taken throw-in played him in.
The deadlock was broken four minutes before the interval, Byrom’s trip on McSheffrey giving away a free-kick 30 yards out.
Baker lifted the free-kick into the box, Clarke towered above the Preston defence to head it down towards the back post where Jennings arrived unchecked and stabbed the ball over the line from four yards.
At the start of the second half, Jack King sliced an ambitious shot high, wide and not very handsome.
The introduction of Jeffrey Monakana in place of Byrom in the 55th minute saw North End move out of their diamond and into a 4-4-2 system.
Monakana’s run created an opening for Wroe as the contest passed the hour mark, Wroe’s shot clipping off a Coventry boot and spinning behind.
North End were back level in the 67th minute, moments after Garner had seen a penalty claim fall on deaf ears after getting a shove in the back.
They won a corner on the right, Welsh swinging it into the middle where Foster rose to meet it on the edge of the six-yard box.
He powered a header goalwards, the ball striking City left-back Blair Adams on its way into the net.
With PNE’s tails up, Holmes tried his luck from distance, only to see his shot sail over the top.
Coventry were a whisker away from regaining the lead in the 76th minute, Baker beating Robertson to a bouncing ball and surging into the box.
The former Southport midfielder put his laces through a right-foot shot which beat Simonsen’s dive but whistled just wide of the far post.
Baker went even closer soon after, McSheffrey having been felled by Welsh 25 yards from goal to win a free-kick.
It was Baker who stepped up to curl it over the wall, the ball clipping the top of the bar and going behind.
North End took full advantage of those let-offs as they went down the other end and went in front with 80 minutes showing on the clock.
Monakana twisted and turned on the right-wing before delivering a low cross to Beavon on the edge of the box.
The front man hit a low shot on the turn which took a big deflection off Wood and wrong-footed keeper Joe Murphy.
In the process of scoring, Beavon took a knock, the goal his last contribution of the night before being replaced by Andy Procter.
But Coventry turned the game completely on its head in stoppage-time as they struck twice to break Preston hearts.
Two minutes of added-on time had been played when substitute Franck Moussa got down the left and put over a cross.
The ball was helped on into the path of Baker at the far post who drove a powerful shot through Simonsen’s legs from an acute angle.
Then 90 seconds later, Baker drove in a shot from 25 yards which Simonsen could only push out.
Three Coventry players were rushing in for the rebound - two of them appearing offside -
and Clarke was first to it to knock the ball over the line from close range.
Coventry: Murphy, Clarke, Wood, Edjenguele, Adams, Baker, Fleck, Bailey (Thomas 53), Jennings (Moussa 75), Fleck, McSheffrey (Elliott 86), Clarke. Unused subs: Cameron, Dunn.
PNE: Simonsen, King, Foster, Cansdell-Sherriff (Robertson 18), Buchanan, Welsh, Wroe, Byrom (Monakana 55), Holmes, Beavon (Procter 81), Garner. Unused subs: Beardsley, Stuckmann.
Referee: Robert Madley (West Yorkshire)