September started slowly due to the international break but would eventually begin with two defeats on the road.
The first came in an enthralling encounter at Upton Park against promotion favourites West Ham. Luke Varney gave Pompey the lead with an early deflected strike but Matt Taylor scored against his former club yet again with a free kick.
Henri Lansbury gave the Hammers the lead with a deflected strike of his own but Steve Cotterill's men hit straight back as David Norris bundled in an equaliser.
The turning point in the game came when Liam Lawrence saw red for stupidly lunging at David Bentley. The hosts took control and a penalty was harshly awarded for handball, which Mark Noble converted.
Carlton Cole then made the victory certain with a looping header but there was more drama as Frederic Piquionne was sent off against his former club for shoving Greg Halford in the face. Halford then scored a penalty with the last kick of the game to make the score 4-3.
The second defeat on the road was on the other end of the spectrum as Pompey were beaten 1-0 by Hull City in a truly dreadful match where the visitors didn't even manage a shot on target at the KC Stadium.
To compound matters, Varney was sent off for a late challenge. Cotterill obviously took the defeat badly as having met him and his team at a service station, the man looked clearly distraught, pacing up and down outside the team coach having apologised to the people who travelled to Humberside to witness such rubbish.
Thankfully, Pompey were back to winning ways a week later against Blackpool thanks to a late stunner from Erik Huseklepp in stoppage time after an even contest.
In a twist of fate the Norwegian scored in stoppage time again in the next home game. Unfortunately, it was in his own net as Peterborough came to Fratton Park and won 3-2.
Bjorn Helge-Riise signed on loan from Fulham and made his debut in that game but Jamie Ashdown would make a huge mistake for the opener which saw him dropped for the nextgame after he somehow juggled Lee Frecklington's long range shot into the back of the net.
Pompey equalised when Gabriel Zakuani turned the ball past his own keeper but Frecklington scored again after more poor Pompey defending.
Benjani equalised in the second half with his only goal of the season before the gutting Huseklepp own goal in stoppage time to put Steve Cotterill even under more pressure.
That poor result brought an end to a difficult month for Portsmouth fans, but the upcoming months would redefine the word "difficult" as a storm was about to hit Pompey hard.