The Spireites were edged out of the Vertu Trophy 4-3 on penalties, following a valiant performance, in a 0-0 draw with Rotherham at the SMH Group Stadium.
Paul Cook made three changes to the last starting XI that narrowly lost 2-1 against MK Dons, on New Year’s Day, as Max Thompson, Dilan Markanday and Kane Drummond made way for Ryan Boot, Ryan Colclough and debutant Bim Pepple.
New signing Janoi Donacien made the bench for the Spireites, along with the returning Ash Palmer.
Boot was required to make a brilliant reaction save to deny Jonson Clarke-Harris on the half-volley, seven minutes in, but the linesman’s flag was already raised so the strike would not have counted.
Pepple had the opportunity to mark his debut with a goal within 20 minutes after Sheckleford’s cross found Armando Dobra, who beat a few defenders in the area to get a shot away, his strike was blocked into the path of the debutant, who could not sort his feet out quick enough to beat Cameron Dawson in goal.
The biggest chance of the game, up to this point, came through Dobra in the 45+1st minute, after he weaved past a few members of the Millers’ defence and attempted to curl an effort into the far corner but, despite beating Dawson, the effort just evaded the post.
The two sides went into half-time deadlocked at 0-0 following an end-to-end first-half of few clear-cut chances. Dobra’s chance, just before the interval, was the closest either team came to opening the scoring in the first period.
The visitors had the first chance of the second half less than five minutes in, via Jack Holmes, who received the ball and drove forward before striking from 30 yards, but his effort kept rising and ended up well over Boot’s crossbar.
Just a few minutes later, Clarke-Harris was played through on goal and cleverly turned away from both Tom Naylor and Jamie Grimes before attempting a shot on goal, but the Spireites skipper recovered to block the chance.
Just past the hour-mark, the ball fell to the Rotherham left-back Reece James, who whipped in a dangerous cross from the left to Andre Green’s head, but the attempt flashed over Boot’s goal.
An almost identical chance to the previous one came for the Millers, less than two minutes later, but this time it was Cohen Bramall’s cross, headed over by Jordan Hugill.
In the 70th minute, there were appeals for a Spireites penalty as Sheckleford fed through the overlapping Dobra, down the right flank, and his low-driven cross was put towards Pepple, but the Canadian appeared to be brought down to be prevented from turning the cross goalward.
Donacien replaced Sheckleford in the 73rdminute to become the second player to make their Spireites debut in this game.
As the clock ticked over into six minutes of added time, Sam Nombe had space to run at the Spireites defence, down the right, and eventually got a shot off at Boot who initially parried the shot and recovered to smother the loose ball, despite Clarke-Harris’ challenge.
The final whistle brought an end to a goalless 90 minutes as a place in the next round of the Vertu Trophy was to be decided with a penalty shoot-out.
Ollie Banks stepped up to begin the shoot-out and scored, despite Dawson getting a touch.
Clarke-Harris levelled the scores with a calmly placed penalty.
Dobra squeezed in the Spireites’ second penalty past Dawson, who got a big hand to the strike.
Nombe sent Boot the wrong way with another calm penalty for the Millers.
Drummond had his penalty saved by Dawson, who guessed the correct way.
Hakeem Odoffin side-footed down the middle to give the Millers a 3-2 lead.
Connor Cook emulated Oddoffin’s penalty, with a side foot down the middle.
Joe Powell sent his penalty into the stand to give the Spireites a lifeline.
Darren Oldaker stepped up to take Chesterfield’s final penalty, which went over the crossbar.
Cameron Humphreys sent Rotherham into the quarter finals of the competition, slotting past Boot, who went the correct way.
The Spireites will return to League Two action on Saturday when travelling to the East coast to face Grimsby Town.
Spireites: Boot, Sheckleford (Donacien 73’), Naylor, Grimes ©, Horton, Oldaker, Mandeville (Akinola 84’), Colclough (Drummond 59’), Hobson (Banks 73’), Dobra, Pepple (Cook 84’).
Unused subs: Thompson, Palmer.
Attendance: 3,517 (943 away)
