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.
13. Mark Hateley
Mark Hateley notched 25 goals in 44 appearances for the Blues during his one and ony season at Fratton Park. After arriving from Coventry for £180,000 in 1983, he was sold to AC Milan for £915,000 in the summer of 1984. Photo: None
14. Christian Burgess
Signed from Peterborough United in 2015 for an undisclosed fee, the centre-back enjoyed five memorable years at Fratton Park. He left on a free transfer in 2020 after Pompey's failed League One play-off semi-final defeat to Oxford. Burgess departed PO4, though with League Two and Checkatrade Trophy winners' medals. | Getty Images
15. Benjani
Tne striker saw his time at Pompey cut short in January 2008 after he was sold to Manchester City - much to his and the fans' disappointment. | AFP via Getty Images
16. Martin Kuhl
The midfielder and former Blues skipper helped Pompey reach the FA Cup semi-finals in 1992 but missed one of the vital penalty kicks that allowed Liverpool to progress to the final. He featured more than 150 times for the Blues before moving to Derby in 1992. Photo: -