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…
9. August 31st - Deadline Day
The Blues completed the shock signing of Millwall wing-back Mahlon Romeo in the final minutes of the transfer window. The summer transfer window was a busy one for Cowley, who brought in 15 new faces over the course of the summer. Photo: Stephen Flynn
10. October 2nd - Best result of the season?
Pompey had gone without a win in League One since August 17th and had alarmingly dropped down the table. But in awful conditions at a sold-out Fratton Park, Cowley’s men thrashed Sunderland 4-0 thanks to a John Marquis double. Many believed this was the start of a turnaround Pompey desperately needed but oh how they were wrong… Photo: Jason Brown
11. October 19th - Ipswich catastrophe
Following a second-half capitulation at the hands of Rotherham the game before, Paul Cook returned to Fratton Park with Ipswich. The Tractor Boys ran riot by scoring four on the south coast which left Cowley’s men 17th in League One. The debacle has since sparked a change in fortunes, though, with Pompey continuing to stay unbeaten in the league since the defeat. Photo: Graham Hunt
12. December 10th - Cowley wins Manager of the Month award
After an impressive November, the Pompey boss was awarded the League One manager of the month award as the Blues rose into the top half following an unbeaten month. The Blues won four of their five League One games, only dropping points in a 1-1 draw against Cheltenham. Photo: Jason Brown