The hosts also suffered a slight setback in their playoff aspirations at the weekend, going down 4-2 to Bromley in a thriller.
Chesterfield's top-seven destiny is still in their own hands heading into the final straight, but Paul Cook's side have given an in-form Dagenham & Redbridge a slight glimmer of hope after their defence was carved open at will by Bromley at the weekend.
A pulsating 45-minute spell saw Laurence Maguire and Tom Denton peg goals back for Chesterfield to see them go into half time with only a one-goal deficit to make up, but Corey Whitely netted Bromley's fourth six minutes after the restart to make sure of the result for the hosts.
With Cook's men simply unable to string consecutive victories together, their spot in the playoffs is far from secure as they sit four points clear of Dagenham, but fixtures with Torquay United and Woking represents an ideal way to round off the regular season.
However, Chesterfield head into Monday's game having only posted two wins from their last seven games in the division - hardly promotion-chasing form - but they have taken 13 points from the last 18 on offer at the Proact Stadium and can still throw the cat amongst the pigeons with regards to the title race.
Similarly, Stockport County are doing their end-of-season goals no favours at present, with the National League leaders suffering a third defeat from four matches when Boreham Wood came to town on Saturday evening.
Elliot Newby's effort in the 94th minute came far too little too late for Stockport to salvage a comeback, as Dennon Lewis and Jamal Fyfield had already made the net ripple for Boreham Wood to leave the title race delicately poised heading into May.
Dave Challinor's side remain in control of their League Two destiny as they remain one point clear of Wrexham at the top of the standings, but the celebrity-owned challengers are only one point worse off ahead of a pivotal top-of-the-table meeting on May 8.
All eyes will be on that encounter next Sunday, but for the time being, Stockport will be desperate to avoid a fourth straight loss away from home against a side who they came back from 2-0 down against to draw 2-2 with on home soil a couple of months ago.
Chesterfield left-back Alex Whittle was reportedly withdrawn injured in the defeat at Bromley and is therefore a major doubt for Monday given the quick turnaround, so Calvin Miller should deputise here.
Danny Rowe and top scorer Kabongo Tshimanga remain on the sidelines alongside Akwasi Asante, whose groin issue was serious enough to keep him out of the Bromley loss, as was Joe Quigley's hamstring problem.
Meanwhile, Stockport County boss Challinor did not report any fresh concerns from the loss to Boreham Wood but is sure to consider some alterations in a desperate attempt to return to winning ways.
Ashley Palmer and Connor Jennings were both early withdrawals in that loss, but having less than two full days to recover may lead Challinor to stick with the duo here. Antoni Sarcevic has also completed a three-game ban, but Will Collar is still on the naughty step.
Chesterfield possible starting lineup:
Loach; Williams, Grimes, Maguire; King, Whelan, Mandeville, Oyeleke, Miller; Tyson, Denton
Stockport County possible starting lineup:
Hinchliffe; Palmer, Hogan, Johnson; Minihan, Sarcevic, Croasdale, Cannon, Rydel; Quigley, Newby
We say: Chesterfield 1-2 Stockport County
Stockport's barren run of defeats cannot go on any longer lest they cede control of the title race to Wrexham, and meeting a Chesterfield side with a host of injury problems could be just the tonic for the league leaders.
The playoff-chasing hosts will put up a good fight nonetheless, but the home crowd at the Proact Stadium have not enjoyed many strong performances on familiar turf of late, and Stockport can take advantage of Chesterfield's injury woes to claim a vital win.