Pompey have been drawn against Arsenal in the third round of the FA Youth Cup.
But first the young Blues must overcome Cheltenham Town in the second stage of the competition if they’re to set up a tie against the Gunners at Fraton Park.
Mark Kelly’s side travel to Whaddon Road on Wednesday night.
Pompey delivered a 5-1 victory over Hereford in the opening round of the tournament last month.
Should the Blues get past Cheltenham, they’ll again face a Premier League club’s Category One set-up in the last 32.
Kelly's youngsters fell to a 2-1 extra-time loss to Leicester in 2017.
And last year, Pompey suffered a heartbreaking 3-2 loss at eventual-winners Liverpool.