Aiyegbeni Yakubu's spot-kick against the post condemned Everton to a UEFA Cup exit after they lost 4-2 in a penalty shoot-out to Fiorentina at Goodison Park Wednesday.
The English Premiership team had taken this last sixteen second-leg into extra-time after goals from Andy Johnson and Mikel Arteta cancelled out the Italian club's 2-0 first-leg lead. But misses by Yakubu and Phil Jagielka in the shoot-out enabled Fiorentina to book their place in the last eight - despite being outplayed by Everton throughout the game.
Having been lucky to escape with just a 2-0 defeat from the first-leg in Florence last Thursday, Everton were fully aware of the task that they faced against Cesare Prandelli's Serie A high-flyers.
The fact that Everton had never previously overturned a first-leg deficit in Europe hardly helped inspire confidence in David Moyes's team, but the Merseysiders certainly threw everything at Fiorentina in an eventful first-half.
Moyes adopted a defensive 4-5-1 formation in the first-leg, relying on Nigeria striker Yakubu to lead the line against the Italians. But after watching that tactic backfire spectacularly in Tuscany, the Everton manager reverted to a two-pronged attack, with England striker Johnson partnering Yakubu.
The pairing caused Fiorentina countless problems in the first-half, backed up by the attacking wing-play of Mikel Arteta and Steven Pienaar. And it was South Africa international Pienaar's cross from the left in the 15th minute that created the chance for Johnson to open the scoring for the home side.
Fiorentina's defence failed to deal with the delivery and Yakubu's near post flick resulted in Johnson bundling the ball into the net with his chest from close range.
Everton sensed a route back into the tie and Spanish midfielder Arteta should have levelled the tie three minutes later when he shot wide from six yards after being picked out at the far post by Joleon Lescott.
Moyes's team continued to pour forward. Arteta had a 25-yard free-kick saved by Sebastien Frey and Leon Osman also tested the overworked Fiorentina goalkeeper. But Prandelli's side knew that one goal would virtually kill the tie off and it required a fine save from Everton's American goalkeeper Tim Howard to keep out Martin Jorgensen's close range volley in the 32nd minute.
Yakubu and Johnson continued to torment the Fiorentina defence, though, and they saw three more good chances go begging before the half-time interval.
The second-half saw Everton step up their bid to score again, however, and they poured forward at every opportunity and they were unlucky not to be awarded a penalty in the 53rd minute when Tomas Ujfalusi handled Pienaar's corner in the six-yard box.
Fiorentina were content to sit deeper and deeper and they merely invited the home side to increase the intensity of their attacks. It appeared only a matter of time before Everton scored again and they were finally rewarded through Arteta's spectacular long-range strike in the 66th minute.
The former Glasgow Rangers midfielder put the tie firmly in the balance by beating Frey with an unstoppable right-foot strike from 25 yards.
But for the French goalkeeper, Fiorentina's hopes would have been buried well before Arteta's goal and he continued to perform miracles, pulling off two incredible saves to deny Yakubu moments later.
Fiorentina remained a threat, though, and they would have put the game beyond Everton had Giampaolo Pazzini's header not been tipped over the bar by Howard in the 76th minute.
Neither side could win the tie in normal time, however, and extra-time brought no further goals, leaving the two teams relying on the lottery of penalties to decide their fate.