After a mixed pre-season and a Community Shield defeat, Pompey began the season with an introduction to Luis Felipe Scolari as the team travelled to Stamford Bridge for an opening day encounter with Chelsea.
17/08/08: Premier League Matchday #1: Chelsea 4 Portsmouth 0
With Harry Redknapp playing Papa Bouba Diop on the right and Younes Kaboul in midfield it only took 12 minutes for a rampant Chelsea to score after Joe Cole slotted past James.
Nicolas Anelka then outjumped the Pompey defence to nod in a second goal from two yards and to add to the misery Frank Lampard scored a penalty on the stroke of half time after Sylvain Distin was harshly adjudged to have handled the ball.
The thumping was underlined when Deco smashed in a long range fourth goal in the last minute of a game where Pompey struggled to cope and the fans were already worrying about the season ahead.
Redknapp knew he had to add to the squad with limited funds and did so by making Jerome Thomas' signing a permanent one which allowded him to bring in Armand Traore on loan from Arsenal.
Traore would make his debut against the Champions the following Monday.
25/08/08: Premier League Matchday #2: Portsmouth 0 Manchester United 1
After the thumping at Stamford Bridge Pompey worked hard against United but fell to a deflected goal by Darren Fletcher in the first half. The Champions could then play keep ball in the second half as they dominated possession and held on comfortably to claim a rare win at Fratton Park.
Pompey were sat at the bottom of the league with a -5 goal difference and then came the news that Niko Kranjcar would be out for at least 2 months after getting injured on international duty.
Linvoy Primus joined Charlton on loan (eventually) and Pompey fans discovered that Vitoria Guimaraes, a club that finished 3rd in the Portuguese league the season before, would be Portsmouth's first ever UEFA Cup opponents.
Pompey were also drawn against Chelsea in the Carling Cup as the fans made their way to Goodison Park for what should have been a very tough game.
30/08/08: Premier League Matchday #3: Everton 0 Portsmouth 3
Jermain Defoe scored Pompey's first goal of the season after turning in the box and firing into the corner. David James then produced a world class save to deny Mikel Arteta what looked a certain equaliser from close range.
Pompey hit the Toffees on the counter-attack and grabbed a second goal when Glen Johnson played a good one-two with Defoe and slotted into the corner past Tim Howard to give Pompey a 2-0 lead at the break.
It looked like Everton would get back into the game when ex-Pompey striker Yakubu stepped up to take an early second half penalty but the spot kick was saved by the outstretched arm of James. Pompey then made sure of the win when Defoe's lob over Howard wasn't claimed to have crossed the line (it did) so Peter Crouch headed in from a yard to make sure.
That resounding victory restored optimism for the season and with the transfer window not shutting until the start of September, there was still time to build a squad capable of challenging for the top five.
Premier League Table on August 31st
15th: Sunderland: 3pts
16th: Stoke: 3pts
17th: Portsmouth: 3pts
18th: Everton: 3pts
19th: West Brom: 1pt
20th: Tottenham: 0pts