The month began with a trip to the home of Volkswagen to take on VfL Wolfsburg who, like Pompey, were in upper-mid table of their league at the time.
04/12/08: UEFA Cup Group Stage Match #3: VfL Wolfsburg 3 Portsmouth 2
Because of ultra tight security outside the Wolkswagen Arena many Pompey fans missed the first quarter of the game in which four goals flew in. Edin Dzeko scored the opener in just 3 minutes.
However, the game was turned on its head when a quick counter-attack led to Armand Traore's shot being parried by Diego Benaglio straight into the path of Jermain Defoe who scuffed in an equaliser.
Arnold Mvuemba gave Pompey the lead three minutes later with a deflected curler but the lead didn't last long as Christian Gentner's harmless looking cross evaded every Pompey defender and found the corner of the net which saw the scores level at half-time.
The second half started well as Niko Kranjcar hit the crossbar with a free kick but disaster struck when David James' woeful backpass was seized by Zvjezdan Misimovic who tapped in an easy eventual winner. In typical jamo fashion he made some amends by saving the Bosnian's penalty after Campbell tripped Dzeko in the box.
The defeat in Wolfsburg coupled with Braga's win at Heerenveen meant that Pompey were out of the UEFA Cup and had to focus on the league. The first match back in domestic action was against West Brom at The Hawthorns.
07/12/08: Premier League Matchday #16: West Bromwich Albion 1 Portsmouth 1
The Baggies took the lead in an awful first half after Chris Brunt's free kick hit the crossbar and Jonathan Greening was there for the rebound. Pompey woke up in the second half but it took a deflected long range screamer from Peter Crouch to beat Scott Carson as Pompey could only take a point from this match against the bottom team in the league.
Believe it or not, but this result took Pompey into 7th in the league. However things would start to go drastically wrong as the Toon circus rolled into town for what looked like a good chance for a win...
14/12/08: Premier League Matchday #17: Portsmouth 0 Newcastle United 3
Rumours were rife before the game that Sacha Gaydamak was in huge debt and star players would have to be sold in January unless a buyer was found. Both Pompey and Newcastle had some great chances in the first half but the Blues fell apart in the second.
After falling behind to a Michael Owen goal, Pompey paid for their profligacy and gung-ho nature to the game and Joe Kinnear's side doubled the lead when we failed to defend a simple throw in which allowed Obafemi Martins to tap in when left alone in the box. Another Geordie counter-attack late on saw Danny Guthrie score a third as the home fans left Fratton Park furious with Tony Adams and the team.
There was some respite for Adams and his team as Heerenveen arrived at Fratton Park for an insignificant UEFA Cup game with only 4th place to play for in the group.
17/12/08: UEFA Cup Group Stage Match #4: Portsmouth 3 Heerenveen 0
Pompey bowed out of Europe on a high as a weakened side comfortably beat the Dutch side courtesy of two Peter Crouch goals and a late Hermann Hreidarsson header.
The first goal came when Crouch headed in Marc Wilson's cross and the lanky striker bagged a second after sliding in Kanu's rebounded shot. The Hermannator added a third on the stroke of full time after heading in Glen Little's free kick as Pompey ended their first ever European campaign.
It was domestic issues that were important after that game but Pompey fans were hit by the news that Lassana Diarra was moving to Real Madrid for £20 million in January. He would make his farewell appearance at the Reebok Stadium.
20/12/08: Premier League Matchday #18: Bolton Wanderers 2 Portsmouth 1
Pompey got off to the worst possible start as the former player curse hit after Matt Taylor volleyed in after 52 seconds following some woeful defending. Ricardo Gardner then lashed in a second after more catastrophic positioning and Pompey were two down after three minutes.
Pompey got one back after Peter Crouch headed in Niko Kranjcar's cross but were second best all game as the scoreline masked Bolton's superiority over a shaky Portsmouth team who also had to clear an effort off the line.
The alarm bells began to ring but Boxing Day saw Pompey's season sink to a whole new level when West Ham visited Fratton Park.
26/12/08: Premier League Matchday #19: Portsmouth 1 West Ham United 4
Pompey took the lead early on when Nadir Belhadj tapped in Glen Little's cross but Jack Collison equalised when his drive evaded every Pompey player in the box and hit the back of the net. Lucas Neill bundled over Peter Crouch in the box but Jermain Defoe's lazy spot kick missed the target and effectively ended his Pompey career.
Carlton Cole would make things worse in the second half when he was allowed an easy stirke on goal and Pompey's gung-ho approach proved to be extremely costly as Craig Bellamy led two West Ham counter-attacks to add to the heavy defeat after Pompey wrecklessly threw men forward. Many of the home fans left early whilst more stayed to boo the team off after a dismal display.
The players had to do some soul searching and find something from somewhere as the next game was a daunting trip to the Emirates Stadium for the final match of 2008.
28/12/08: Premier League Matchday #20: Arsenal 1 Portsmouth 0
A defensive Pompey unit had a great chance to take the lead early in the game when Peter Crouch hit the post with a header but we were let off when Emmanuel Adebayor raced clean through on our goal only to be denied by some excellent covering by Campbell and Distin.
Gooners and Pompey fans united in abusing Spurs and Harry Redknapp but the home support grew frustrated as they couldn't break down the blue resistance. Unfortunately David James flapped at a free kick which allowed William Gallas to head in a winner in the last ten minutes as Pompey were beaten by Tony Adams' old club.
Papa Bouba Diop was also stretchered off during the match and would not play for Pompey again for the rest of the season. The worst news was that what looked a promising season at the beginning had turned into a relegation battle as Pompey were just 3 points clear of the drop and only 5 from the bottom.
And things would get worse in 2009...
Premier League Table on December 31st
10th: West Ham: 25pts
11th: Bolton: 23pts
12th: Portsmouth: 23pts
13th: Man City: 22pts
14th: Newcastle: 22pts
15th: Sunderland: 22pts