The third round clash with the Gunners could hardly have arrived at a more challenging time for John Mousinho’s men, who are decimated by injury.
That provides a challenge for the Blues boss, as he looks to put out a competitive side with obvious Championship survival considerations, too.
Here’s how we think the Pompey boss will go, as he takes on the potential top-flight champion’s huge array of talent.
5. CB Conor Shaughnessy
Interesting one this, after his first start in four months on New Year's Day. Could be a case to save Shaughnessy for Sheffield Wednesday, but he'll want to play - so we're leaning towards him starting but coming off as the afternoon progresses. Photo: Graham Hunt
6. LB Swanson
One for the full-back to savour as he faces the club he came through the ranks with. Now a man when arriving at Pompey as a boy - and will want to show the Gunners his progress. Photo: Graham Hunt
7. Andre Dozzell
Big afternoon for the midfielder who will, no doubt, have to produce some high mileage to contain Mikel Arteta's side. Photo: Graham Hunt
8. CM: Marlon Pack
After watching Pompey take on the Premier League big boys as a child, the Buckland boy should now get the chance to lead out his hometown club against one. | Graham Hunt