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.
1. From left: Sean Raggett, Guy Whittingham, Jed Wallace and Jermain Defoe
From left: Sean Raggett, Guy Whittingham, Jed Wallace and Jermain Defoe | National World/Getty Images
2. Guy Whittingham
The striker was sold to Aston Villa for £1.2m in 1993 after scoring 109 goals in 188 appearances for Pompey following his arrival on a free transfer in 1989. | Getty Images
3. Matt Clarke
The popular centre-back was sold to Brighton for £3.4m in 2019 after 174 appearances and nine goals for the Blues. Not a bad deal for a player who initially joined on loan from Ipswich, before joining as part of the deal that took Adam Webster to Portman Road. | Getty Images
4. Noel Blake
The defender played 173 games for Pompey and scored 14 goals. He helped the Blues win promotion from the old Division Two in 1987, but within a year he was on Leeds United's books | National World Photo: National World