Two years ago this tie looked dire on paper as Ipswich were languishing in mid-table after selling their best players in the previous summer whilst Pompey's problems were well documented.
Indeed, the game itself wasn't a great spectacle as Ipswich had plenty of chances in a game they deserved to get something from. However, despite their dominance it was Dario Silva who headed the only goal of the game to put Pompey through to the next round.
Fast forward two years and the prospects of both teams are much different now...
Ipswich are undefeated at home this season, winning 11 of their 13 games at Portman Road. I've watched them a couple of times this season and they play some good football and really put teams under pressure.
However, Pompey currently have the best away record in the entire country having won 8 times on the road if you include cup competitions. This is also the last time we will see Sulley Muntari, John Utaka, Papa Bouba Diop and Kanu before they jet off to Ghana, so they are probably going to start tomorrow.
I hope Harry plays our strongest side available, although it wouldn't surprise me to see some of our fringe players given a run out considering that we've played so many games in a short space of time. Jim Magilton is likely to field his strongest side to take the game to Pompey.
Harry's selection might also indicate who's on their way this month too. The valuation of our players could decrease if they are cup-tied, so it'll be interesting to see if anyone who usually makes the squad is left out.
I think that we can go there and win so long as we give Ipswich the respect they deserve and play a strong side. Nobody will fancy a replay given our crisis at home and Ipswich's awful away form so hopefully we can get the job done tomorrow.
It should also be a very good game of football on paper and one I look forward to. I just hope our journey to Wembley isn't over before it has even begun.
Predicted Starting Line-Ups
Ipswich
GK: Neil ALEXANDER
RB: Luis Castro SITO
CB: Jason DE VOS
CB: Alex BRUCE
LB: David WRIGHT
RM: Danny HAYNES
CM: Owen GARVAN
CM: Tommy MILLER
LM: Gavin WILLIAMS
CF: Alan LEE
CF: Jon WALTERS
Bench: Shane SUPPLE, Fabian WILNIS, Sylvain LEGWINSKI, Liam TROTTER, Pablo COUNAGO
Pompey
GK: David JAMES
RB: Glen JOHNSON
CB: Sol CAMPBELL
CB: Sylvain DISTIN
LB: Hermann HREIDARSSON
CM: Richard HUGHES
CM: Papa BOUBA DIOP
CM: Sulley MUNTARI
RWF: John UTAKA
LWF: Matthew TAYLOR
CF: KANU
Bench: Asmir BEGOVIC, LAUREN, Niko KRANJCAR, BENJANI, David NUGENT
Pundit Watch
Lawro: Draw (1-1)
Sky Sports: Away Win (1-3)
My Prediction: Away Win (1-2)