Former Blues skipper Tom Naylor settled matters with a first-half header which deservedly gave Paul Cook’s impressive non-leaguers victory.
It was a season’s worst display from John Mousinho’s men, particularly in the first half, and here are our Pompey player ratings...
13. Portsmouth forward Paddy Lane (32) shoots early on during the FA Cup match between Chesterfield and Portsmouth at Technique Stadium, Chesterfield, United Kingdom on 5 November 2023.
Paddy Lane 's early goal attempt is blocked by ex-Pompey captain Tom Naylor. Picture: Simon Davies/ProSportsImages Photo: Simon Davies
14. Sean Raggett - 6
(Replaced Regan Poole on 11 mins) Strong as ever and produced one lovely turn in the first half to lose a player. Fortunate not to concede a penalty in the second half. Photo: Jason Brown
15. Gavin Whyte - 4
(Replaced Tino Anjorin on 44 mins) Could not inspire the Blues with a desperately disappointing performance, particularly in the second half. Has found it tough to shine at Pompey and this was another forgettable display. Photo: Jason Brown
16. Zak Swanson - 5
(Replaced Joe Rafferty on 46 mins) Introduced as Rafferty was on a yellow and did okay, but barely raided that right flank. Can be one of the few who can escape criticism, defending well. Photo: Jason Brown