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...
1. Chesterfield's Liam Mandeville (left) and Portsmouth's Jack Sparkes battle for the ball during the Emirates FA Cup first round match at SMH Group Stadium, Chesterfield. Picture date: Sunday November 5, 2023. PA Photo. See PA story SOCCER Chesterfield. Photo credit should read: Nigel French/PA Wire RESTRICTIONS: EDITORIAL USE ONLY No use with unauthorised audio, video, data, fixture lists, club/league logos or "live" services. Online in-match use limited to 120 images, no video emulation. No use in betting, games or single club/league/player publications.
Chesterfield's Liam Mandeville tries to get the better of Jack Sparkes. Picture: Nigel French/PA Wire Photo: Nigel French
2. Will Norris - 5
Early scare when his kick was blocked by Grigg and there will be questions over his decision to come and punch the ball from the free-kick which Naylor headed home. Positioned himself well to claim other shots, but largely had little to deal with. Photo: Jason Brown
3. Joe Rafferty - 5
(Replaced by Zak Swanson on 46 mins) Saw very little of him attacking down the right, very much restricted to defensive duty. Did okay overall and assured as ever, but was taken off at half-time over concerns over being on a yellow card. Photo: Jason Brown
4. Regan Poole - 6
(Replaced by Sean Raggett on 11 mins) Injured his left leg when outmuscled off the ball by Will Grigg and was forced off. Photo: Jason Brown