August proved to be a difficult month as Portsmouth struggled to adapt to life in League Two. September wasn't any easier although the month began with joy in Southampton's favourite cup competition; the Johnstone's Paint Trophy.
A trip to Plainmoor was first up and after failing to score for 90 minutes, the match against Torquay went straight to a penalty shootout. If Yassin Moutaouakil is to be remembered for anything other than being one of Pompey's worst full backs in recent years it would be for his cheeky Panenka chip to send his team through to the next round of the JPT.
Pompey's first league assignment of the month took them to Whaddon Road to face Cheltenham Town with ex-Pompey-and-Robins-boss Steve Cotterill watching.
It took just five minutes for Patrick Agyemang to give the visitors the lead but the hosts equalised when Jermaine McGlashan rounded the onrushing John Sullivan and put the ball into an empty net.
Johnny Ertl stunned everyone by actually scoring a goal and celebrated just like someone who had never scored and Pompey had plenty of other chances to win the match.
However, just like the previous two away games, Whittingham's team surrendered a 2-1 lead with McGlashan capitalising on more poor defending to tap in a harsh stoppage time equaliser. The Robins did bundle a third goal in at the death but thankfully it was ruled out for offside.
Another away trip followed as Portsmouth fans travelled to Burton-on-Trent to play the Brewers for the very first time.
Two scrappy goals gave Pompey a commanding lead with Ricky Holmes tapping in the first after Agyemang's initial header was saved by Jordan Pickford. The Burton keeper saved a Holmes shot later in the second half only for Simon Ferry to slide in the rebound.
Moutaouakil was dismissed late on for stupidly lashing out and Pompey did concede once again in injury time as Zander Diamond bundled the ball past Sullivan but it didn't matter as the Blues finally earned their first away win of the campaign.
John Marquis was loaned from Millwall and Ryan Bird left for Havant & Waterlooville temporarily as Pompey looked to build on their victory with another against Fleetwood Town.
Unfortunately Whittingham's men didn't put up much of a fight against the Cod Army who won the match thanks to an unfortunate own goal from Sonny Bradley as Jamille Matt's strike ricocheted off the onrushing Sullivan and then the defender before finding the back of the net.
David Connolly was made part of the coaching staff ahead of Pompey's final match of the month and it would prove to be a harrowing experience at York City.
This match would be John Sullivan's worst nightmare. He spilled a free kick to allow Wes Fletcher a tap in just three minutes into the game but the worst was to come in the second half after Jed Wallace had equalised with a truly superb solo goal.
The hapless Sullivan dropped the ball from a corner straight to the feet of Lewis Montrose who was grateful for the easiest goal he'd ever score. Pathetic attempts at defending allowed Ryan Jarvis to slot in a third and Fletcher to head in a fourth and whilst Marquis scored a good consolation goal late on, this was truly a game to forget for all Portsmouth supporters.
That mauling left Pompey on just nine points from nine games which was hardly promotion winning form and some fans began to question Guy Whittingham's future as Portsmouth manager heading into October.