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.
21. Alan Biley
Biley scored 65 goals in 119 games for Pompey before his departure to Brighton in 1984. Speaking in Neil Allen's 'Played Up Pompey' in 2015, the former forward said: 'I never wanted to leave Pompey, I wanted to cement myself in folklore, to be one of the club greats. You don’t know anything about Pompey until you drive onto that island, you haven’t got a clue. When you do, it grabs you forever. 'My belief was I would have rotted under Alan Ball if I hadn’t left, but by going to Brighton it finished my career anyway because the heart had been ripped out of me.' | National World Photo: None
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22. Jermain Defoe
The controversial front man left Pompey after less than a year at Fratton Park - reuniting with former Blues boss Harry Redknapp at Spurs. With 17 goals in 34 appearances, it's no wonder many were heartbroken by his prompt exit and return to North London. | Getty Images
23. Jamal Lowe
Plucked from non-league football, the forward spent two-and-a-half successful years at Fratton Park, winning both the League Two title and the Checkatrade Trophy. The lure of Wigan Athletic proved too much, though, in the summer of 2019. | Getty Images
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24. Ron Saunders
Saunders remain's the third-highest scorer in the club’s history, netting 162 times in 261 appearances afterbeing recruited in September 1958. Arriving from Division Four side Gillingham for £10,000, the powerful centre-forward scored at least 20 times in four of his six full campaigns. Saunders left in August 1964, moving to Watford in a £15,000 deal following a bitter fall-out with manager George Smith. | Getty Images