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 wanting a new challenge elsewhere.
It’s a painful circumstance to watch as it unfolds and can stir up emotions long after the said player is left.
As a result, it’s probably a subject matter that some don’t want to be reminded off. For others, though, they’ll happily reminisce about players who got away - as @Pompey_Goals found out when he asked Blues supporters on X, formerly Twitter, ‘Which was the first player Pompey sold that really hurt you?’
The response from the Fratton faithful was impressive, with a whole host of names offered up. So much so that we asked @Pompey_Goals to run a story on the names mentioned.
So here’s 18 former Pompey players fans wished had never been sold without evening mentioning Mick Quinn, Benjani, Vince Hilaire, Noel Blake, Steve Claridge, Peter Mellor, Jed Wallace and Matty Taylor!

13. Barry Horne
The midfielder was snapped up from Wrexham for £60,000 in 1987 and went on to make 76 appearanced for the Blues. Pompey made a huge profit on the Welshman in 1989 after accepting a bid of £700,000 - the only problem was it was Southampton who had the offer accepted. @TonyDogTrainer wrote: 'Barry Horne. Favourite player but then jumped ship to the Scummers'. | National World

14. Gary O'Neil
The big Fratton Park favourite was sold to Middlesbrough for £5m by Harry Redknapp.@Thomas_2791 said on X: 'I’ll never forgive Redknapp for O’Neil being sold.' | Getty Images

15. Russell Hoult
The keeper was sold to West Brom in January 2001 for £450,000. @AndyHaynes147 wrote: 'Russell Hoult to WBA sticks out for some reason. Felt like we’d never get a keeper that good ever again.' | Getty Images

16. Colin Garwood, left, with Ray Crawford
The striker was in prolific form during the 1979-80 season, establishing himself as the Blues’ 17-goal leading scorer in their bid to win promotion from Division Four. However, in February 1980, he was controversially sold to Aldershot – to the shock of the Fratton faithful. @Limmy05 commented: 'Colin Garwood to Aldershot ..... Luckily we scrapped up'. | National World

