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...
. 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
. 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
. 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
. 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
. Conor Shaughnessy - 6
Pompey’s best defender and retained that characteristic composure, although one loose pass did present Colclough with a decent second-half chance. Overall, however, a decent display, particularly after the reshuffle following Poole’s exit. Photo: Jason Brown
. Jack Sparkes - 4
(Replaced by Abu Kamara on 60 mins) Looked well off it and one of his last contributions was the covering Jacobs beating him too easily inside Chesterfield’s box in a great position. Took a knock after declining to use his right foot to play a pass and came off shortly afterwards. Photo: Jason Brown
. Joe Morrell - 7 - Man of the Match
Tried his best to get Pompey going and, more than many of his team-mates, showed character, fight and a determination frustratingly lacking from others. Comfortably Pompey’s man of the match. Photo: Jason Brown
. Alex Robertson - 4
Probably his most ineffective Pompey display yet, particularly in the second half when the team needed his inspiration. Disappeared from action at times rather than dictating player and will be a match to learn from. Photo: Jason Brown
. Terry Devlin - 4
(Replaced by 60 Kusini Yengi on 60 mins) No heroics this time from the teenager, who struggled to get into the match. Nonetheless, plenty of effort and endeavour from the youngster, even if a quiet match. Photo: Jason Brown
. Paddy Lane - 5
Had a bright first half but quickly faded after the break, unable to make things happen. Was eventually swopped to the left wing with Kamara moving to the right, only to produce some dreadful crosses when Pompey needed him most. So disappointing. Photo: Jason Brown
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