The Spireites go from top of the league on Saturday to bottom on Tuesday as they take on Blackpool at Bloomfield Road in midweek.
The match comes in a key week for the Spireites as they try to get back on track with two away games at two struggling sides, with Crewe Alexandra to follow on Saturday
Winger Gboly Ariyibi has jetted off to join the USA under 23 squad and will miss the next three Chesterfield games, while striker Byron Harrison will also be out for six to eight weeks with a knee injury picked up in last week's reserve team win against Scunthorpe United.
Manager Dean Saunders said in his pre-match press conference that striker Lee Novak is likely to miss the next two or three games through injury - the on-loan man not travelling to Blackpool on Tuesday with the squad.
Spireites striker Mani Dieseruvwe serves the second and final game of his suspension after his second red card of the season at Coventry City ten days ago.
Blackpool defender Tom Aldred was replaced in Saturday's 2-0 loss to Shrewsbury Town and will miss out with a hamstring injury, with the match at the New Meadow containing an away performance manager Neil McDonald described as "rock bottom".
Veteran midfielder David Norris made his first Tangerines start in the match and the former Ipswich Town and Leeds United man brings experience and an eye for goal to the team.
While the Spireites late conceding woes in their last three home games will need little reminding of to Spireites supporters, Saunders's side have fared reasonably well on their travels, winning on two of their four league trips this campaign.
Blackpool - fresh from Championship relegation last season - prop up the League 1 table this season, and have struggle particularly on their own patch. The Seasiders have picked up just a single home point in four games at Bloomfield Road, though that draw was earned in their last home outing against Barnsley.
With incoming manager McDonald doing his best to weld together a virtually new squad since his June arrival, the Tangerines have improved in recent weeks with hopes now higher of a climb up the table.
From the Dugout
Looking ahead to the match, Saunders knows that despite the Tangerine's disappointing run of early season results they are a side well-capable of picking up and starting some good form.
He said: "They're struggling to get results at the minute and we need to make sure that if they are struggling they're still struggling after the game.
"We can't let them get a win and I would imagine that if they can get on a run - and they will do because their coach is good and experienced - they can do well. Sometimes it takes a month, sometimes a year or two.
With both teams much-changed over the summer the manager is focused on getting his side back into the winning frame of mind on Tuesday evening.
"They have a new team, as do we," he said. "We've picked up some points early on which we deserved, but we've let a few points slip which is disappointing.
"I still realise that what we have here isn't quite right but the points we are picking up gives me more time to sort out the things that are wrong.
"We'll get a team out there that will try and win the game, that's the only thing I'm thinking about."
Those not able to get to Bloomfield Road can still follow all of the action. There will be live commentary on PlayerHD and social media has everything covered as well.
There will be minute-by-minute coverage on Twitter as well as updates on Facebook and Instagram throughout the evening, followed by comprehensive post-match content.