Chris Porter netted the winning penalty for Oldham Athletic, as they edged past Chester in Fourth Round Qualifying to set up an FA Cup First Round tie with Wrexham.
It wasn't for a lack of effort from the hosts. A second-half of extra-time strike from Kevin Roberts had put Chester on the brink of a famous FA Cup victory.
With seconds left to play and the First Round in their sights, the dream of a cross-border FA Cup clash with rivals Wrexham slipped away in cruel fashion.
Looping a header into the far-corner of the Chester goal, Mike Fondop's 119th-minute equaliser ensured the tie would be decided by a penalty shootout.
In the end, there would be no cup-upset for Chester. Instead, the hosts were left with a crushing feeling of what could've been, as both Roberts and Kole Hall slipped in their penalty run-ups, sending the ball over the crossbar in the process.
On balance, Chester may feel hard done by. They had fought hard throughout the clash, but were unable to see the victory acrss the line.
For Oldham, their battles will be fought elsewhere this season, yet avoiding an FA Cup upset will offer new boss David Unsworth a glimmer of confidence after a testing start to life in management.
Sensing their team were on the verge of something special, the Chester supporters set out on creating an atmosphere only ever reserved for FA Cup nights under the lights at this level. What followed was an intriguing battle between National League Oldham and sixth tier Chester.
Perhaps unfair to label Oldham as the 'Goliath' in this clash between heavy favourite and underdog, the EFL League Two drop-outs were certainly fancied to progress into the First Round Proper of this season's FA Cup.
But, as has been the case for much of its 151 year history, the FA Cup once again showed its disregard to superior league rankings.
The game turned after a late tackle from Jordan Clarke on Anthony Dudley - a challenge which sparked a scuffle on the pitch and tensions on the bench.
At this point, Oldham had already broke the deadlock and Chester had been comfortably second-best. Finding it difficult to wrestle possession back from their National League opponents, the home side could do little about Ben Tollitt's opening goal after nine minutes.
Finishing off a blistering Oldham counter attack, the former Wrexham winger's effort deflected off the covering Chester defender, before looping over Harry Tyrer in the Chester goal.
It had been no less than Oldham deserved, with the Latics coming close to taking the lead inside a minute when Mike Fondop broke in behind the Chester backline, but was unable to latch on to a searching long ball.
Prior to Clarke clattering into Dudley midway through the first half, sparking the touchline scuffle in the process, it had been a rather subdued night for the Chester faithful.
The pre-match festivities had been dampened by the early Oldham goal, but with the impromptu scrap, the Deva Stadium found its voice.
Rejuvinated, a roar of encouragement met every Chester attack, with the hosts registering their first shot on target via a drilled Kieran Coates strike from 25-yards out.
Called into action for the first time, a strong right hand from Oldham goalkeeper Magnus Norman was enough to tip Coates' goal-bound effort around the post.
From thereon in, the tempo was set. While the hosts may have trailed at the break, a Chester equaliser felt inevitable.
It arrived through Kurt Willoughby, who was allowed to ghost into the Oldham penalty area, before nodding home at the back post and restoring parity.
Tails up, Chester could've won the tie in normal time. Having tormented the Oldham defence all evening, Willoughby found Kole Hall inside the penalty area, but the 24-year-old's first-time effort was smothered by Latics goalkeeper Norman.
As the clock trudged towards 90 minutes, a medical emergency in the stands temporarily halted play. For the first time in a long time, a hush swept around the Deva Stadium, before a ripple of applause to thank the medical staff who dealt with the problem.
Responding well to the stoppage in play, Chester carried their momentum from the second half of normal time over to the first half of extra time, eventually taking the lead stylish fashion nine minutes after the restart.
Weaving through the Oldham half, Roberts tucked a well-struck right-footed effort into the far-right corner, evading the outstretched arm of Norman and sending the Deva Stadiun into raptures.
It would prove nothing more than a moment in time for the Seals faithful, whose dreams would be dashed with one minute of extra time to play, before defeat in the penalty shootout.
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