On Friday 13th, are these the unluckiest moments in Pompey’s history?

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Pompey's Jack Whatmough heads at goal against Oxford United. Picture: Joe Pepler/Digital South.

Picture gallery: Oxford United 3 Pompey 0

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Pompey have had plenty of ups over the years but, like any other club, there have been downs for fans to endure.

On Friday 13th, we ask whether these might be the unluckiest moments in the club’s proud history.

October 20, 1928: A very bad day at the office. Pompey travelled to Filbert Street and left having suffered what is still their worst defeat. Leicester City walloped them 10-0, with the midlands club’s record goalscorer Arthur Chandler scoring six goals. Legend says that just after Chandler scored his fifth goal, five swans flew over Filbert Street. A few minutes later a sixth swan flew overhead, to which Chandler promptly responded by scoring his sixth goal of the afternoon.

April 1934: Jimmy Allen was a superb defender whose sale to Aston Villa financed the building of the North Stand at Fratton Park. With him in the back line, Pompey had every chance of overcoming Manchester City to win the FA Cup for the first time in their history. They led 1-0 but with seventeen minutes to go at Wembley, Allen was injured and had to leave the pitch. While Manchester City had the man advantage, Matt Busby took a throw in and played the ball to Brook, who passed to Tilson to score. City soon added a winner and Pompey would have to wait another five years before lifting the cup.

March 26, 1949: Peter Harris is Pompey’s all-time record goalscorer, but his inexplicable miss in the FA Cup semi-final at Highbury put paid to Pompey’s excellent chance of becoming the first team of the 20th century to win the Double. The favourites were trailing 2-1 to Second Division Leicester (already becoming something of a bogey team) when Harris dragged a shot wide with an open goal before him. The 60,000 spectators were still trying to work out why when Don Revie bagged his second goal to give Leicester a surprise 3-1 win.

1966: With manager George Smith famously observing that there was nothing but fish in the sea around Portsmouth, Pompey abandoned their youth system and reserve team in a move that many fans believe set the club back for years. Among the young professionals shown the door at Fratton Park was a defender called Mick Mills - he of 40+ England caps.

April 1992: The depth of the crossbar prevented Pompey from reaching Wembley with a famous win over Liverpool. Having been clawed back to 1-1 four minutes from the end of extra time in the semi-final at Highbury, they played superbly to hold the mighty Reds at 0-0 in the replay at Villa Park. Late in the game, Alan McLoughlin had a chance to score the winner, but his shot cannoned back off the underside of the bar. Liverpool held their nerve in a penalty shootout in which Pompey couldn’t hit a barn door - and the dream of Wembley was over.

May 1993: With Guy Whittingham scoring a record 42 league goals, Pompey looked certain for promotion to the Premiership. But the sendings off of Guy Butters and Paul Walsh in a 4-1 disaster at Sunderland set up the chance for West Ham to sneak above Pompey by winning at an already promoted and some say not particularly battling Swindon Town. Pompey were pitched into the play-offs against, yes, Leicester City again. A 1-0 loss in the first leg was followed by a 2-2 draw at Fratton Park in which Ian Ormondroyd scored a patently-offside goal and Pompey missed out by a whisker.

2003: Pompey turned down the chance to sign Didier Drogba for just £3.5m. Harry Redknapp flew to Lyon to watch Drogba for Guingamp in Le Championnat and was desperate to sign him up. But Pompey deemed the price too high, so Harry signed Teddy Sheringham on a free transfer from Spurs instead. Drogba went on to Chelsea to enjoy one of the most-successful Premiership careers of all time. He always seemed to score against Pompey, including bagging the only goal in the 2010 FA Cup final.

September 2003: Pompey missed the chance to ruin Arsenal’s Invincibles season - thanks to Robert Pires. The Frenchman - roundly booed in every subsequent appearance at Fratton Park - ran into the penalty area and flicked his right foot at the stationary leg of Dejan Stefanovic, creating the illusion of a foul. Referee Alan Wiley fell for it - and Arsenal’s successful penalty earned a 1-1 draw to keep their unbeaten season on track.

November 2008: Pompey’s first season in major European competition threw up a dream home tie with AC Milan. Inspired by a frenzied crowd, Pompey went 2-0 up against the Italian giants but, with a few minutes left, substitute Ronaldinho curled in a superb free kick. Then, late into injury time, veteran Filipo Inzaghi struck at the Milton End to deny Pompey what would arguably have been their greatest-ever victory,

*Is there an unlucky moment that still haunts you as a Pompey fan? Please let us know by commenting on this story