Sunday's game may be all-or-nothing for Pompey but it's also a huge match for Tottenham too. I caught up with season ticket holder Dave Winchester and asked him some questions ahead of the game.
With Pompey being bottom of the league and having allsorts of problems off the pitch, you must surely fancy your chances this Sunday?
We certainly do and it seems like the majority of football fans around the country do as well, it's just asking for "the magic of the cup" and the upset many would like to see this weekend!
We have the better team on paper and our league position emphasizes this, but it's 90 minutes to play and anything can happen. Admittedly, 90% of Tottenham fans are going into the match as if we've already won it, a bit like when Liverpool sent out the email for the next round of the Cup before they were knocked out of it, an upset is there to happen!
What's more important to Tottenham? Winning the FA Cup or qualifying for the Champions League next season? What would Spurs fans prefer?
Ask any Spurs fan this question and the answer is both! I would love the trophy in the cabinet, we get mocked for counting the Carling Cup as being a major trophy over the past few years so it would be nice to add the FA Cup to this list.
It is also a trophy very much associated with our history having already won the cup 8 times already and with the 3rd best record in the history of the Cup, it would be brilliant to win it again as it's been while!
Despite all of that though, I believe more Spurs fans would prefer a Top 4 finish and potentially Champions League Group Stages. I don't think we would embarrass ourselves at that level although we would certainly find it difficult to get to the knockout stages. But we would also be advertising ourselves as a club on the up and so may be able to attract some bigger players to help ourselves out next season.
How has Younes Kaboul settled in back at White Hart Lane? Are you concerned that he can't play against us at Wembley?
Poor. Very poor. I was one of very few who said when he left he has potential, he looks like he lacks a leader in the defence and I feel he showed some progress at Portsmouth, a lot of progress since his previous spell at White Hart Lane.
He has come back and been played central midfield and tried to play defensive and looked lost, he then went to central defence and looked clumsy, back to midfield and played a simple game and he did well but not really "top 4 challenging" well!
He will be missed with our current injuries to King, Dawson and Woodgate. We are lacking in the back 4 with Walker also being cup-tied and Corluka looking doubtful.
How are some of the other Pompey old boys performing this season?
Kranjcar has been brilliant, our signing of the season. His pace worried many fans at the beginning of his Spurs career but he has shown that not being as rapid as Lennon isn't a problem when you have the vision and footballing brain he has. He's had a patch of a few poor games but seems to be coming back to form just at the right time.
Crouch has been ok. We've resorted too much to the obvious, hoof to Crouch! It hasn't worked very often and it's no surprise, defenders are generally well built and will out muscle him in the air. The times where we've tried to play football with him he's performed well, just unfortunate for him that Pavlyuchenko has found his shooting boots and has effectively put Crouch on the bench recently.
Defoe started the season very well, scoring for fun and then hit a patch where he couldn't score and became sloppy, shooting from 25 yards and hitting Row Z in the Upper Tier regularly! He's had a few cracking matches this season and despite him not scoring as often as we would like you will often hear a sigh of relief when his name is read out on the team sheet. He's very much a form player but also a match winner.
And how do Tottenham fans view Harry Redknapp after what has been a very good season so far?
Harry has done a very good job. He's not been as rash as when he started here, if a mistake was made he would take that player off almost instantly, he is a little more lenient now and has let the likes of Pavlyuchenko prove himself in the team which looked unlikely after some of the press. He also hasn't said his wife could finish some of the chances our current strikers have missed which is a positive!
Pompey signed another former Tottenham man this January in Ricardo Rocha. What did Spurs fans think of him when he was at White Hart Lane?
A player who we signed and constantly wondered why he wasn't started and when he did he usually put in a reasonable performance but never really looked comfortable in our team.
It can't have been good for him sitting out of the game for so long, I don't think anyone outside the staff at White Hart Lane could give you a review of him, he was that rarely seen in Spurs colours!
What are the main strengths and weaknesses of this Tottenham side?
Strengths: Attacking. We look like we can score at every attack, we are putting in more crosses compared to last season and our strikers are reacting much better. Wing play has been brilliant and the addition of Bale overlapping down the left has been amazing. Bale has been our best player of the new year.
Weaknesses: Defence. Dawson has been brilliant, Bassong has been very good, Corluka and Bale have been very good. Gomes has been outstanding, potentially our player of the season.
It all sounds good! The problem is that we seem to defend well for 80 minutes in a game and Dawson and Bassong are occasionally turned far too easily. We still haven't learnt to defend crosses and set pieces either! Gomes has improved on them but the defenders still don't seem to man mark very well. I would say to Portsmouth, ping the ball into the box at every opportunity, the same advice I would have given the past 2 or 3 seasons!
I would also say a central midfield lacking Palacios and Huddlestone is one with little strength and possibly little defensive steel. Modric gets back but doesn't get his foot in too often.
What is your view on the current situation at Pompey? Are there any players in the squad that you think could cause Tottenham some problems or is this going to be a walkover for you?
The Prince would certainly love to prove a point against us on Sunday! He is very unpredictable and another player who maybe didn't get the best of chances at Tottenham to prove his point. I also think Piquionne is one to watch, he seems very tricky and likes to run at players, two of the attributes I hate to see against the likes of Bassong who can commit too early. Michael Brown can also bring a yellow card out against any player! He has a player's attitude you love in your team and hate to play against!
Predict the outcome of the match.
Portsmouth 0-2 Tottenham. Kranjcar and Pavlyuchenko with the goals.
Finally, a good luck from me and I'm sure the majority of the Tottenham fans. You won't see many away fans applauded like Pompey fans were a few weeks ago at White Hart Lane.
"Pompey Til I Die" was applauded by all 4 stands and then after 95mins when White Hart Lane was almost empty and the Portsmouth fans came out with "Is there a fire drill?," it went down well with us still in the South and East stands! Hopefully see you back in the top flight soon.