None of us have escaped the pain of seeing a firm Fratton favourite leave for pastures new - whether it be through financial issues at the club, a player falling out of favour with the manager, an offer proving too good to be true, or the player himself just a new challenge elsewhere.
It’s a painful situation to watch as it unfolds - and can continue to stir up raw emotions long after the said player is departed.
As a result, it’s probably a subject matter that some don’t want to be reminded of. For others, though, they’ll happily reminisce about players who got away - as The News found out when we asked our followers on Facebook to name the player they were most heartbroken to see leave Pompey.
The response was impressive, with a whole host of names offered up. So here’s 27 former Pompey players who broke the fans’ heart upon their Fratton Park exits.

25. Neil Weld
The midfielder enjoyed a three-year and 138-game stint at Fratton Park that brought with it the 1982-83 Third Division title. That was secured during his first season with the Blues, following his £83,500 switch from Reading in 1982. Webb proved an instant firm favourite with the fans, which will explain why there was anger when he was sold to Forest for £250,000 in 1985. The move earned him a personalised message from the 657! | National World Photo: The News archive

26. Paul Merson
Paul Merson's Pompey stay was short but sweet. With 12 goals in 48 appearances, he was a key figure in Pompey's 2002-03 First Division title-winning season. He never played for the Blues in the Premier League, though - instead signing for Walsall after some unforgettable scenes at Fratton Park. | National World

27. John Aloisi
The Aussie forward netted 29 goals in 66 matches for the Blues following his arrival from Italian side Cremonese in August 1997. He was sold to Coventry for £690,000 in December 1998 at a time when Pompey were in financial trouble. | Getty Images Photo: Getty

28. Matt Taylor
Taylor was part of the Pompey team that secured promotion to the Premier League in 2003, after helping Harry Redknapp’s side secure the old First Division title. He would go on to make 113 top-flight appearances for the Blues before being sold to Bolton for an undisclosed fee in 2008. | Getty Images