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.
9. Sean Raggett
Pompey fans were heartbroken when the PO4 cult hero wasn't offered a new deal at the end of the Blues' 2023-24 League One title-winning season. The centre-back was allowed to leave Fratton Park on a free transfer after 238 appearances and 17 goals. | National World
10. Pedro Mendes
A £2m January 2006 signing from Spurs, the Portuguese is still remembered fondly at Fratton Park following that goal against Man City that sparked the Great Escape. The midfielder was allowed to join Glasgow Rangers for £3m in the summer of 2008 - just weeks after helping Pompey win the FA Cup. | Getty Images
11. Darren Anderton
Signed as an apprentice, Anderton went on to play 77 games for Pompey before Spurs signed him for £1.75m in 1992. | Getty Images
12. Jed Wallace
The forward enjoyed a four-year stint in the Pompey first-team after emerging through the club's youth ranks. His meteoric rise in a struggling Blies side came as no surprise, with Wallace scoring 30 goals in 121 appearances before being snapped up by Wolves for £250,000 in 2015. The forward is also a former The News/Sports Mail Pompey Player of the Year winner. | Getty Images