The opportunities for the Spireites to snap their losing run are coming quickly, with a trip to MK Dons next on the agenda as the club look to self-right themselves.
In their way stand a struggling and manager-less MK Dons side, also in the bottom four and without a Stadium MK win to call their own in the league this campaign, following Championship relegation last term.
Spireites fans can no longer buy tickets for the match at the Proact, however, tickets are on sale on matchday at Stadium MK. Further details can be found here
Danny Wilson spoke in his pre-match press conference on the liklihood of injured players returns on Tuesday night. The manager stated that striker Ched Evans is 50-50 for the match, with both he and hamstring-strain victim Jon Nolan to be assessed ahead of the game.
Wilson confirmed that full-back Liam Graham has a cartilage injury and will miss a few weeks, with 'keeper Tommy Lee still feeling pain in his shoulder as he works his way back from a serious shoulder injury.
The Dons' major talking point of the weekend comes not from between the white lines, but just to the side of them, with former England captain Steven Gerrard reportedly offered the position of manager at Stadium MK over the weekend. With the situation remaining unclear it seems - at the time of writing - that caretaker Richie Barker will be in charge for a third game when the Spireites come to town.
Barker, if he is in charge, is not expected to face any new injury concerns for the match, with Samir Carruthers and Joe Walsh back in the side in the weekend's goal-less draw at Bristol Rovers.
Eight games into their losing run, and the Spireites have still been unable to bring an end to it. The latest attempt, the 2-1 Saturday loss at Fleetwood, was typical: creating chances, not taking them and being made to pay for defensive lapses at the other end.
Something may have to give at Stadium MK on Tuesday night, however. The Spireites may not have won away from home but the Dons have yet to win at home in the league this season, and have gone over six weeks since their last Sky Bet League 1 success.
Like their Spireites, the Dons have tasted FA Cup success in the midsts of their barren run, with a 3-2 win over Spennymoor Town in round two their only home win thus far in 2016/17.
From the Dugout
Wilson told PlayerHD before the game that both sides will be going into the game thinking they might have the edge due to their opposition's record, but that his side can prevail - if they take their chances.
"If we play like we can and as we did for long periods on Saturday we know we can make opportunities," he explained. "Whether we can take those opportunities is going to be the difference between the two teams.
"At home they seem to be struggling this year. They have an array of talent and a big squad and sometimes you just can't put your finger on what's causing it.
"They've got too much talent for us to presume it'll be an easy game because they've not won at home. They might go the other way and think that because Chesterfield have not won away from home it'll be easy for them. Let's hope we can shock them a bit."
You can follow every kick of the action from Stadium MK on Tuesday night, even if you're not there in person. We have live commentary on PlayerHD, minute-by-minute coverage on Twitter and the usual updates, stats and images across Instagram, Facebook and the official website.