Having sold Lassana Diarra to Real Madrid and having signed Nadir Belhadj permanently from Lens in December, Jermain Defoe then told Peter Storrie he wanted to leave and he wouldn't feature in Pompey's first FA Cup match since the final back in May 2008.
03/01/09: FA Cup Round #3: Portsmouth 0 Bristol City 0
Pompey began their FA Cup defence with a dire draw with the Robins. Sylvain Distin had a couple of efforts cleared off the line and Niko Kranjcar missed a free header but the rest of the match was a dull affair as the Championship side held the cup holders to a replay.
Jermain Defoe completed his return to White Hart Lane to be reunited with Harry Redknapp but Gary O'Neil wouldn't be reunited with Pompey after Middlesbrough rejected a bid for him.
Because of the freezing conditions, Pompey's match against Manchester City was called off and so the next game would be the FA Cup replay at Ashton Gate.
13/01/09: FA Cup Round #3 Replay: Bristol City 0 Portsmouth 2
The home fans were angry eight minutes before the break as it looked like Peter Crouch had handballed an incoming corner in the box but it wasn't given and moments later he gave Pompey the lead following a quick counter-attack.
David James kept Pompey in the game with a string of saves and the cup winners would secure passage into the fourth round when Niko Kranjcar tapped in Nadir Belhadj's cross in the 88th minute. Jamo even saved Nicky Maynard's last minute penalty to keep a clean sheet.
The next match was one that Pompey fans had been looking forward to since October as the team travelled to White Hart Lane for an encounter with Harry Redknapp's Spurs.
18/01/09: Premier League Matchday #22: Tottenham Hotspur 1 Portsmouth 1
An eventful first half saw Jermain Defoe miss a sitter early on whilst both Gomes and James had plenty of work to do to keep the scores level at the break. Come the second half and David Nugent picked the perfect time to score his first Premier League goal with an angled strike from distance.
The travelling fans taunted Redknapp but were faced with the inevitable when Defoe struck the equaliser and celebrated like it was the best goal he'd ever scored. Darren Bent missed a free header at the death as Pompey finally got a result at the Lane.
Tony Adams finally got his man by signing Jermaine Pennant on loan from Liverpool but played him in centre midfield in the match which was possibly the worst result of the season...
24/01/09: FA Cup Round #4: Portsmouth 0 Swansea City 2
Pompey were humiliatingly dumped out of the competition they won last year by the team that were knocked out the same year by Havant & Waterlooville. What made it worse is that the first goal was scored by on-loan Scummer Nathan Dyer after he got the better of Sol Campbell.
The second came just before the end of the first half after Belhadj's rash challenge on Jordi Gomez that looked outside the box was judged to be inside and Jason Scotland scored the resulting penalty.
Pompey tried hard to get back into the game but Dimi Konstantopoulos would not be denied his clean sheet, producing save after save to make sure Swansea upset the odds and the home fans left Fratton Park extremely angry after the cup winners were knocked out by lower league opposition at home.
Tony Adams knew that the midfield had to be improved quickly and to solve the problem he signed Hayden Mullins from West Ham for £1 million and loaned Pele from FC Porto. The former would become the main target for criticism for the rest of the season whilst the latter never made a single appearance for the blues.
After that FA Cup humiliation the league situation was also about to get worse with the visit of Champions League chasing Aston Villa to Fratton Park.
27/01/09: Premier League Matchday #23: Portsmouth 0 Aston Villa 1
Emile Heskey scored the winner at Fratton Park for the second time in a season after nobody read Gabriel Agbonlahor's flick to the Villa striker who slotted past James early on. Agbonlahor missed a golden opportunity to double Villa's lead but it was all Pompey from then on.
Despite all the possession, Pompey couldn't carve out any clear chances and the game was effectively lost when Nadir Belhadj was given his marching orders after receiving a second yellow card for arguing with the officials, having been lucky to only get a yellow for an earlier kick on Craig Gardner.
That defeat had Pompey fans seriously worried about relegation and those worries would deepen on the last day of the month as Pompey travelled to West London.
31/01/09: Premier League Matchday #24: Fulham 3 Portsmouth 1
Fulham's impressive home record was under no threat after Andy Johnson beat the offside trap and slotted past James after 14 minutes but we were denied a blatant penalty after John Paintsil took out David Nugent in the box.
The game was over when Pompey committed defensive suicide by trying to play the offside trap in their own half which meant a long ball upfield to Erik Nevland resulted in the Norweigan striker running the whole second half of the pitch and finishing past James.
Nevland then added insult to injury by turning in the box and firing in a third and although David Nugent headed in a consolation there was no time to mount a comeback and Pompey fans left the Cottage wanting Tony Adams out.
With just one win in 11 league games Pompey had slid to 15th position in the table, just one point above the relegation zone and no sign of the slide halting. February was going to be a pivotal month in Pompey's season and everyone, including the Portsmouth board, knew it.
Premier League Table on January 31st
13th: Sunderland: 26pts
14th: Tottenham: 24pts
15th: Portsmouth: 24pts
16th: Stoke: 24pts
17th: Newcastle: 23pts
18th: Blackburn: 23pts