The Blues may be the league’s form side but it's a tough assignment as they take on the Tractor Boys, who are also in good form themselves under new boss Kieran McKenna.
McKenna’s men are unbeaten in eight and were touted as the division’s best side by Lincoln boss Michael Appleton, after his side were defeated 2-0 on Tuesday night.
Danny Cowley has to consider how best to contain the big spenders, who could afford to name the likes of Conor Chaplin, James Norwood, Joe Pigott and Macauley Bonne on the bench at Portman Road last time out.
There are Pompey selection considerations all over the pitch, including who starts at left wing-back and in the middle of midfield, but particularly who partners George Hirst up front.
Here’s how we think Cowley will go in Suffolk.
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17. Sub 5: Ryan Tunnicliffe
Will go very close to starting and, if he doesn't, likely he'll return at Plymouth next week. Photo: The News
18. Sub 6: Michael Jacobs
What a boost it will be to see the man who was becoming so important before injury struck return. Photo: The News
19. Sub 7: Tyler Walker
Got his goal on Tuesday, but will it be enough to keep him in the team? Likely to be a close call between the loanee and Aiden O'Brien. Photo: The News