Chesterfield’s dismal record in the FA Cup continued on Saturday as Paul Cook’s side went down 3-1 at home to League Two rivals Southend United.
The Spireites have made it through to the third round of the competition only once since reaching the semi-final stage in 1997, when they finally succumbed to Bryan Robson’s multi-millionaire Middlesbrough in a replay.
But they looked on course to add to the bitter-sweet memories of five years ago, when they reached the third round after an incident-filled tie against Droylsden, when Tendayi Darikwa ghosted in at the far post to give Cook’s men an early lead.
The winger, in his first start for Chesterfield since away at Bristol Rovers towards late October, did his chances of starting against Oldham Athletic in the Johnstone’s Paint Trophy no harm with a tireless performance in front of Drew Talbot.
The way Chesterfield carved the visitors open with consummate ease was a joy to behold and showed how effective they can be when on song. However, rather than it being a platform to build on, the goal signalled the start of a Southend fightback.
Anthony Straker was a thorn in the Spireites’ side all afternoon and gave glimpses of how devastating he could be with the ball at his feet, or in the air, in a first half which saw Phil Brown’s Shrimpers grow in confidence, as they went about seeking revenge for a league defeat on the same ground in August.
The hosts had already shown their vulnerability on crosses when Barry Corr tested Tommy Lee, in the Chesterfield goal, within seconds of the kick-off. And the approach proved fruitful for Southend when Ben Coker’s corner was met by Mark Laird at the near post to level matters.
A familiar name around Chesterfield, Kevan Hurst, who was not only born in the town but played more than 50 league games for the club during an 18-month spell from 2005-07 while on loan from Sheffield United, had a day to savour for the visitors.
He was equally as useful on the right as his teammate, Straker, was on the left, and the two combined to put Southend into the lead, the latter glancing a header into the bottom corner of the net as Chesterfield stood and watched.
Two crosses had yielded two goals and the Spireites could have found themselves even further in the mire when a corner from the right prompted Corr to fall to the floor after a tussle with Sam Hird in the second half.
The man in the middle, Mick Russell, had a clear view of it and was on hand to award the penalty.
Chesterfield felt aggrieved at Newport when a penalty kick was awarded against them. This week they could have no complaints.
The only positive to come out of the incident was Lee’s outstanding save from Corr’s spot-kick which acted as a shot in the arm for the hosts. It ignited the crowd and the team responded with a flowing move from left to right which brought the best out of Lee’s opposite number, Dan Bentley, who acrobatically parried Armand Gnanduillet’s header to safety.
Talbot had earlier clipped the bar with a header.
And so it was left to Hurst to have the final say after a penetrating run from Straker left a sea of blue shirts in his wake. The midfielder shaped to shoot with his right before turning back on his left and buried the ball, as well as any lingering hopes the Spireites may have had of making it into Sunday’s third-round draw.
Once again the manner of the defeat, rather than the result itself, was a difficult pill to swallow for Chesterfield, who have shipped six goals in two matches against teams with similar ambitions to themselves in their respective league campaigns.
There was further cause for concern when Gary Roberts hobbled off with a suspected hamstring injury, which looks likely to rule him out for a testing Christmas period.
*Chesterfield (4-2-3-1): Lee 6; Talbot 6, Hird 5, Evatt (c) 5, McFadzean 6 (Doyle 74); Ryan 6, Banks 7; Darikwa 7, O’Shea 6 (Richards 68), Roberts 6 (Humphreys 15, 5); Gnanduillet 5. Subs not used: Chapman, Togwell, Devitt, McSheffrey.
*Southend (4-2-3-1): Bentley 6; White (c) 6, Kiernan 6 (Phillips 62), Prosser 6, Coker 6; Laird 7, Timlin 6; Hurst 8, Clifford 7 (Thompson 82), Straker 8; Corr 7. Subs not used: Smith, Eastwood, Reid, Payne, Edwards.
Goals: Darikwa 4; Laird 12, Straker 17, Hurst 85.
Bookings: Evatt 6; Hurst 57, Coker 65.