Pompey have been forced to settle for a League One play-off place this season.
After falling to a 3-2 defeat against Peterborough on Tuesday, it put paid to the Blues’ automatic promotion hopes.
There have been several moments throughout the campaign which fans pinpoint why Kenny Jackett’s troops missed out on a top-two berth.
Here’s a look at five games Pompey will have been frustrated to have dropped points…
Poor Oxford performance – January 19, 2019
Kenny Jackett’s side travelled to the Kassam Stadium in January needing a response after losing to Blackpool at Fratton Park a week beforehand.
Despite the U’s sitting in the relegation zone, the Blues delivered an under-par performance and fell to a 2-1 defeat.
The visitors deserved to go into half-time two goals behind, with Cameron Brannagan and James Henry netting for Oxford.
And while Brett Pitman notched a consolation goal, Pompey ultimately deserved to make the journey back down the A34 empty-handed.
The Southend collapse – February 16, 2019
Pompey were cruising to victory in front of the Sky Sports cameras at Roots Hall.
After 31 minutes, Bryn Morris, Ben Close and Oli Hawkins put the Blues 3-0 up and three points looked a near certainty.
But somehow Pompey would only return to Fratton Park with a point.
Simon Cox reduced the arrears to give Southend a lifeline before half-time.
And the Shrimpers striker would go on to complete his hat-trick and leave Jackett’s men stunned.
Held by struggling Pirates- February 19, 2019
Pompey were lucky to escape with a point against Bristol Rovers.
If it wasn’t for Jonson Clarke-Harris sending a second penalty into orbit after scoring one before half-time then the Blues would have fallen to a 2-1 loss.
But with Pompey without a victory in six matches, it really was a must-win game against a side battling the drop.
Bogle’s missed Barnsley penalty – February 23, 2019
A goalless draw against a promotion rival would be a good result in normal circumstances.
But not when there’s a missed penalty in a game few goalscoring chances were created.
Viv Solomon-Otabor superbly stood up Barnsley right-back Dimitri Cavaré and won Pompey a penalty.
With no Brett Pitman or Gareth Evans on the pitch, Omar Bogle stepped up to take the spot-kick.
However, the on-loan Cardiff striker’s effort lacked conviction and was easily saved by Tykes keeper Adam Davies.
That Peterborough moment – April 30, 2019
It is a whirlwind few minutes which will long be remembered by the Fratton faithful.
Solomon-Otabor thought he’d given Pompey the lead against Peterborough but was flagged offside.
And two minutes later, it was the Posh who put the ball in the back of the net.
Some argued Solomon-Otabor was to blame for not holding his run, while other fans felt Brett Pitman should have shot himself instead of passing.
Regardless of who to blame, it’s a moment that could prove so costly if Pompey aren’t promoted this season.