The first hurdle to overcome are Leeds United who redefine the term "crisis club". Since their relegation from the Premier League they've lost a play-off final, been relegated again, almost gone extinct due to bad financial management and now are having to claw their way back up the third tier after being handed a 15 point deduction for their troubles. And to add insult to injury, they've had to tolerate Dennis Wise as their manager.
Still, that doesn't seemed to have stopped the team performing on the pitch as the points deficit is now down to 6 after making a habit of scoring late goals to win their first three league games, so we cannot take them too lightly.
Both sides are set to rest key players for the "more important" league games ahead and so for Pompey to charge adults to fork out £25 to watch what could easily be mistaken for a lower league fixture is completely ludicrous.
Football is expensive enough as it is, so we don't need these huge extra costs to burden us, especially with other Premier League clubs charging £15 for a league game. Even a special offer would have been nice but once again it looks like the fans will continue to be priced out...
For those who do decide to turn up, it's important to get behind the players as if it were a league game because this fixture is more important than some fans regard it as.
After all, if we're aiming for Europe then winning the Carling Cup is one way of achieving that target and with the big four refusing to take the competition seriously, we stand a good chance of going far this year if the draw is kind to us for once. Ironically, our last League Cup tie at home was back in 2004 against Leeds!
The likes of Jamo, Sol and Kanu are set to be rested whilst Linvoy Primus could make his comeback game along with other fringe players looking to prove themselves. Despite their lowly status, Leeds still have a few recognisable names including Tore Andre Flo and David Prutton.
Just how many players Harry decides to leave out is anyone's guess but I expect the eleven players picked to get the job done against a side who will not want to risk their key players as they look to defy all the odds and win promotion from League One.
Predicted Starting Line-Ups
Pompey
GK: Jamie ASHDOWN
LB: Djimi TRAORE
CB: Linvoy PRIMUS
CB: Noe PAMAROT
RB: Martin CRANIE
LM: Matthew TAYLOR
CM: Richard HUGHES
CM: Arnold MVUEMBA
RM: Gary O'NEIL
CF: BENJANI
CF: David NUGENT
Bench: David JAMES, Hermann HREIDARSSON, Sean DAVIS, Franck SONGO'O, KANU
Leeds United
GK: Casper ANKERGREN
LB: Jamie CLAPHAM
CB: Rui MARQUES
CB: Ben PARKER
RB: Scott GARDNER
LM: Ian WESTLAKE
CM: Johnathan HOWSON
CM: Johnathan DOUGLAS
RM: Sebastien CAROLE
CF: Tresor KANDOL
CF: Tore Andre FLO
Bench: Matt HEATH, Andy HUGHES, Robert BAYLY, David PRUTTON, Jermaine BECKFORD