After a torrid 2010, Pompey fans were hoping for a far better 2011 but the new year couldn't have started any worse as the New Year's Day trip to Vicarage Road was one to forget.
Andrew Taylor scored one of the Championship goals of the season to set the ball rolling for the Hornets and then poor defending saw Watford hit Pompey with two goals on the break from Marvin Sordell and Danny Graham.
Greg Halford was then sent off in stoppage time for aggressively pushing his face into Taylor's just to compound the visiting fans' misery.
Two days later Hull came to Fratton Park and were dominated in the first half yet still took the lead through Jimmy Bullard's penalty. Lawrence scored a spot kick of his own in the second half to level things and it looked like Pompey were going to turn things around.
However, two quick-fire sucker-punch goals followed as both Matty Fryatt and Nick Barmby fired past Ashdown after catching the Pompey defence off guard.
Halford headed in a corner to give the home fans some hope but despite the relentless pressure, Hull held on for the win.
Steve Cotterill's next task was to motivate his side for the FA Cup third round tie at League One leaders Brighton. Pompey fans travelled in their numbers to the horrible Withdean Stadium and were in for a difficult evening.
Dave Kitson was sent off for punching Adam El-Abd in an off-the-ball incident and it wasn't long before a ten man Portsmouth side were ran ragged by the Seagulls with Chris Wood's tap in and Ashley Barnes' penalty giving the hosts a comfortable lead.
There was a small glimmer of hope when Tom Kilbey scored his only goal for Pompey in stoppage time but Brighton went straight down the other end and scored through Francisco Sandanza to cap a truly miserable day.
With injuries and suspensions hitting the squad hard, Steve Cotterill was grateful to borrow Ritchie De Laet from Manchester United and he would go straight into the starting line-up for the match at promotion chasing Nottingham Forest.
Kanu surprisingly gave Pompey the lead after taking what seemed like forever to pick his spot after he had rounded Lee Camp in the Forest goal.
Pompey dug deep and it seemed like a win at the City Ground was on the horizon but Ibrahima Sonko's own goal late in the match undone all of that hard work.
Then, to make matters even worse, Marcus Tudgay fired in a winner in the last minute of stoppage time to break the hearts of every Pompey fan as their team had fallen to yet another defeat.
The next match was a home encounter against Leeds United and it'll be remembered for two bizarre floodlight failures. Joel Ward had given Pompey the lead with a drive from 25 yards in a first half that the home side dominated.
But Leeds equalised just after half time as Luciano Becchio tapped in a loose ball from a free kick. Utaka then got the better of his marker to give his side the lead again only for the defence to concede just minutes later when Davide Somma scored with his first touch.
Then came the floodlight incidents that happened due to electrical work being carried out in the Fratton area and NOT because the Portsmouth owners hadn't paid the bills! The match ended in a draw which didn't do much for Pompey's prospects.
Steve Cotterill bolstered the squad with the loan signing of Jonathan Hogg from Aston Villa and he went straight into the side for Pompey's final game of the month with Eddie Howe's Burnley.
In what was one of the worst performances of the season, Jay Rodriguez gave the Clarets the lead following some poor defending but Utaka equalised with what was his last goal for the club.
More comedy defending ensued as failure to clear the ball in the box led to Dean Marney scoring with an overhead kick. Pompey had no answer to that goal and were booed off at the final whistle after yet another defeat.
As transfer deadline day loomed, it was revealed that John Utaka had been sold to Montpellier for less than £500,000 - a paltry return on the £8 million Harry Redknapp paid for him in 2007.
There were no major arrivals or departures on the last day of the month, meaning Steve Cotterill was lumbered with three players he couldn't play in Michael Brown, Richard Hughes and Tal Ben-Haim who had returned from a loan spell at West Ham.
That brought to an end a very difficult month for Portsmouth Football Club both on and off the pitch. There was little action in the transfer market and the team had only taken one point from fifteen and had been knocked out of the FA Cup to lower league opposition.
It seemed like February would be a make or break month in Portsmouth's season...