The former Arsenal man won The Cup on four of those occasions, scoring a goal in 2002, winning man-of-the-match in 1998 and tasting his first victory as a 20-year-old in 1993.
Manchester United v Arsenal
The FA Cup
Sixth Round Proper
7.45pm, Monday 9 March 2015
Old Trafford, Manchester
Winners receive £360,000 from prize fund
Live on BBC
And as his old club prepare for Monday evening’s Sixth Round tie with Manchester United at Old Trafford, Parlour was this week reflecting on the one that got away when the Gunners lost to the Reds in the Semi-Final of 1999.
With both clubs competing for the league title, the sides met in a replay at Villa Park where a last-minute Dennis Bergkamp penalty was saved by United ‘keeper Peter Schmeichel before Ryan Giggs scored one of the greatest Cup goals in extra time to send them to The Final.
United then went on to pip them to the Premier League title, before adding The FA Cup and European Cup to complete a unique treble, something which Parlour believes Arsenal should have prevented.
"It was one of those situations when we were absolutely distraught afterwards," he told TheFA.com
"It was a replay, it went to extra time, they had a last-minute penalty which Dennis Bergkamp missed with the last kick of the game.
"It wasn’t just that, but I’m sure we would have won the league that year as we only lost it by one point that season.
"It’s all about momentum in football and sometimes it’s fate, Manchester United went on to win the treble.
Parlour and Arsenal team-mate Freddie Ljungberg with The Cup in 2002
"Sometimes a little bit of luck can go your way and change a season, but losing that Semi-Final was a real low point.
"Luckily enough, I’ve had plenty of high points too and played in five FA Cup Finals.
"The one we should have won was against Liverpool in 2001, but the other four were all really competitive and tough.
"It was always a special trophy for me as a kid, in our household, my mum and dad made us watch every single game, whoever played.
"So to win my first one as a kid in 1994 was special, and then to get man-of-the-match against Newcastle in 1998 when we won the double was too.
"And then there was the goal against Chelsea in 2002 and the last one against Southampton in 2003."
Those four winners’ medals are what Parlour looks at to remind him of the good times and after Arsenal’s Cup success last season, he hopes the current squad do the same.
Their victory over Hull City in last year’s Final brought them the first silverware for nine years and this season could offer them a similar opportunity if they can beat Louis van Gaal’s side.
Watch highlights of the 2014 FA Cup Final at Wembley as Arsenal pick up the trophy
"Everybody knew the pressure that Arsene Wenger was under after no trophies for nine years, so it was a big trophy for the club and the team," he added.
"It was the first one they had won together and I promise you, that first one is the hardest as a group.
"There’s the prospect of a Semi-Final waiting for them, so they’ll fancy their chances, it’s a big trophy and they’ll have enjoyed every minute after winning it last season.
"I’m sure they’ll want more of that so it’s a big game, Manchester United will be challengers and Old Trafford is always a tough place to play, it’s going to be a tricky game for Arsenal.
"But Arsenal have the players to really affect games, people like Sanchez and Cazorla.
"This FA Cup is massive, especially for Arsenal as it’s the only trophy they can really win and it’s the same for Manchester United."
