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…
1. January 23rd - Pompey mauled by the Tigers
It was a feisty game as league-leaders Hull took on third placed Pompey at Fratton Park. Two Jack Whatmough own goals helped the Tigers maul Kenny Jackett’s side 4-0. The result overshadowed the then perceived impressive signings of Charlie Daniels and George Byers from Shrewsbury and Swansea respectively. Photo: Kieran Cleeves
2. March 13th - Papa John’s Trophy defeat
Saturday March 13th will go down as one of the worst days in the recent history of the club as Pompey were dominated by League Two side Salford City in the EFL Trophy final at Wembley. Man of the Match Craig MacGillivray ensured the tie finished goalless after 120 minutes but Jackett’s men lost 4-2 on penalties. A result which would prove costly. Photo: Bryn Lennon
3. March 14th - Kenny Jackett's sacking
Following Pompey’s embarrassing Trophy final defeat, boss Kenny Jackett was sacked by the board following a poor run of form which led to just one win in eight before his departure. A relief for many Pompey fans who had called for Jackett’s head at the start of the season. Photo: Joe Pepler
4. March 19th - Danny Cowley appointed head coach
Former Lincoln and Huddersfield boss Danny Cowley was appointed five days after Kenny Jackett's departure, fending off bookies' favourite Daniel Stendel. Danny was joined by brother Nicky as the pair joined on a deal until the end of the season - a deal which was made permanent following the conclusion of the 2020-21 season. Photo: JPIMedia