But the Blues make the long trip to the Riverside Stadium buoyed by a couple of decent league performances against Leeds and Luton.
It won’t be easy against Michael Carrick’s side, however, who are expected to push for promotion this term.
With Sammy Silvera unavailable against his parent club and new faces in the building in keeper Nicolas Schmid and midfielder Abdoulaye Kamara, there’s plenty for John Mousinho to ponder.
Here’s how we think Pompey will line up as they travel to Teesside.
1. Pompey predicted line-up
Matt Ritchie is pushing for his first Pompey start at Boro. | The News
2. GK Will Norris
Here comes the competition for Norris in the shape of new boy Nicolas Schmid. Undroppable after his clean sheet and heroics against Luton last week, however. | National World
3. RB Jordan Williams
Looks to be in front of Zak Swanson in the right-back pecking order at present. | National World
4. CB Conor Shaughnessy
Important at the back and threatening in attack as Shaughnessy led by example against Luton. | National World