The Blues go into the new year sat ninth in League One – six points off the play-offs.
But what could have been if Danny Cowley’s men had made the play-offs at the end of last season?
We’ve highlighted 13 key events that have shaped the Pompey first team’s 2021…
5. May 9th - Final-day heartbreak
Following Cowley’s appointment, it was evident that performances had improved but it wasn't enough as a failing group of players missed out on the play-offs on the final day of the season. His side lost 1-0 to Accrington at Fratton Park on the final day of the season as Cowley’s men ended the campaign eighth in League One. Photo: Joe Pepler
6. May 10th - Cowley signs long-term deal
The day after their Accrington disappointment, Danny and Nicky Cowley signed long-term contracts to stay on the south coast, signalling the start of a new era at Fratton Park - much to the relief of many Pompey fans. Photo: Joe Pepler
7. July 1st - Out of contract players leave
Ben Close, Ryan Williams, Tom Naylor, Jack Whatmough and Craig MacGillivray, some of Pompey’s standout performers over the course of the season, all left Fratton Park following the expiration of their contracts. Much to Cowley’s frustration, some of the players’ increased wages couldn't be struck and the boss was left with just a handful senior players in the squad. Photo: Joe Pepler
8. August 17th - Top of the pile
Cowley’s new-look side burst out of the blocks at the start of the campaign, beating Fleetwood, Crewe and Shrewsbury to sit top of the pile after three games. This would send a signal out to Pompey’s League One rivals who had a slow start to the new season. However, soon the tide would turn. Photo: Jason Brown