It was a moment Joe Mason won’t want to be reminded about.
The Wolves loanee had a gilt-edged opportunity to open up his Pompey goal account during the Checkatrade Trophy clash at Crawley on Tuesday.
With the Blues leading 1-0 on 89 minutes, Anton Walkes was brought down inside the area to win his side a late penalty.
Mason stepped up to take the spot-kick – but was left blushing.
The forward’s effort was well off target, not just sailing over the bar but going out of the Broadfield Stadium.
Only 484 Blues fans were in attendance to witness the penalty first hand, but the video replay was quickly doing the rounds on social media.
However, Mason isn't the first player donning the star & crescent to make a hash of a spot-kick – and certainly won’t be the last.
On Facebook page Portsmouth FC – The News and Twitter account @pompeylive, we asked fans if they can remember any penalties that were worse than Mason's.
And there were plenty of responses.
Members of the Fratton faithful picked out Conor Chaplin's miss at Stevenage during the 2016-17 title-winning campaign.
With Paul Cook’s side trailing 3-0, the striker had the chance to grab a late consolation for the visitors.
However, Chaplin proved too clever for his own good.
He chipped his effort down the middle, but failed to fool Chris Day. The keeper didn’t move from his spot, easily swallowing up Chaplin’s shot.
Twitter user @PompeyInUganda wrote: ‘Conor’s chip down the middle at Stevenage... keeper just stood and caught it. 3-0 down it was a painful one in front of the away fans.
On Facebook, Shaun Nicholls added: ‘Chaplin v Stevenage was horrendous.’
Another poor miss from the 12-yard spot in recent seasons was Jed Wallace's against Exeter during 2014-15.
With the game goalless, the midfielder had the opportunity to give the Blues the lead after Matt Tubbs was brought down in the area.
Wallace stepped up in front of the Fratton End but blazed his shot over the bar.
Luckily for the fans’ favourite, he atoned his mistake by netting a 91st-minute equaliser to deliver his side a 1-0 victory.
An infamous Pompey penalty miss fixed in the minds of supporters is Jermain Defoe’s in the 2008-09 season.
There were plenty of talk regarding the striker potentially departing Fratton Park to again link-up with Harry Redknapp, who’d left for Tottenham Hotspur two months earlier.
On Boxing Day, Tony Adams’ men hosted West Ham. With the game poised at 1-1, Pompey won a penalty and Defoe stepped up to take it.
However, the England international’s effort was off target and the hosts went on to fall to a 4-1 defeat against the Hammers.
Defoe went on to move to White Hart Lane when the January transfer window opened.
Earlier that season, the Blues visited Wembley for the third time in five months to face Manchester United for the Community Shield.
The game finished goalless after 90 minutes, leading to penalties.
Pompey fell to a 3-1 shoot-out loss, with Lassana Diarra, Arnold Mvuemba and Glen Johnson all missing.
Defoe had netted the Blues’ second spot-kick.
@J_Man90 wrote on Twitter: ‘All the penalties in the Charity Shield game against Utd.’
@ttwood_sam added: ‘Glen Johnson’s penalty in the Charity Shield nearly left Wembley.’
On Facebook, Colin Jackson mentioned were Kevin-Prince Boateng’s against Chelsea in the 2010 FA Cup final.
How different that game could have been if the Ghana international didn’t have his 54th-minute effort saved by the legs of Petr Cech.
Wayne Rickard nominated Alan Biley’s against Bournemouth in the 1982-83 season.
He said: ‘THE worst ever.’
Matt Dunn put up a spot-kick Mick Quinn missed against Plymouth.
‘Micky Quinn Plymouth away can’t remember the year,’ he said.