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.

5. Lassana Diarra
The French midfielder is considered by many to be the best player ever to play for Pompey. His time at Fratton Park was shortlived, however. After signing for Pompey from Arsenal in January 2008 for £5.5m, the FA Cup winner was snapped up by Real Madrid in January 2009 for a cool £20m. Diarra played only 32 times for the Blues but he left a lasting impression. | National World Photo: IAN KINGTON

6. Dave Kemp
32 goals in 64 appearances following his 1976 move from Crystal Palace says it all. The forward was Pompey's top scorer between 1976-77 and 1977-78, but stayed at Fratton Park for less than two years after compelting move to Carlisle. Kemp was inducted into the Pompey Hall of Fame in April 2016 | National World

7. Gary O'Neil
The midfielder was sold to Middlesbrough in 2007 for £5.5m after 192 appearances for the Blues and helping Pompey win the First Division title in 2003. | Getty Images

8. Mick Quinn
The striker was a huge success at Fratton Park after Alan Ball paid Oldham £150,000 for him in March 1986. After 54 goals in 121 appearances, though, he was swapping Fratton Park for St James' Park in 1989, after Newcastle had a £680,000 bid accepted for the Pompey forward. | National World Photo: a