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.
17. Mick Kennedy
By far the most popular player among our Facebook poll. Mick Kennedy was the hard man's hard man. When talking about proper Pompey enforcers, there's only one place to start. Scully made 149 appearances between 1984 and 1988, where he could lay claim to being the toughest midfielder in the game. A 1986-87 promotion winner, the midfielder was soon sold to Bradford due to the Blues' financial problems. | The News
18. Arjan De Zeeuw
De Zeeuw featured 115 times for Pompey - 68 of which came for the Blues in the Premier League. Signed from Wigan on a free transfer, the defender was also key member of Harry Redknapp’s 2002-03 First Division title-winning side, making 35 league starts that memorable campaign. Returned to Wigan in 2005. | National World Photo: Neal Simpson
19. Paul Walsh
The stylish frontman broke Pompey hearts when he signed for Manchester City in 1994 after 91 appearances and 21 goals during his first spell at Fratton Park. | National World Photo: The News archive
20. Conor Chaplin
The Pompey Academy product's 2019 exit still hurts the Fratton faithful - especially as he's curerntly plying his trade in the Premier League with Ipswich Town. | Getty Images