The Spireites will go hunting for lucky number seven at London Road as they look to bring their poor recent streak of six straight league losses to an end.
New manager Danny Wilson will be in the stands for the game, watching on before taking the reigns for the match with Coventry two days later.
Standing in the Spireites' way are sixth-placed Peterborough United, on a hot-streak since Graham Westley took over as manager in September.
Tickets are available on matchday at London Road, with these prices: adults £23, over 60s and 18-21 £14 and under 18s £10.
Caretaker manager Mark Smith commented in his pre-match press conference that he expects 'keeper Tommy Lee and striker Lee Novak to be fit and ready to go on Boxing Day.
Lee had pulled up during the first half of Saturday's match with Bradford City but managed to finish the game, while Novak had missed the game in its entirety with a minor thigh complaint.
The Spireites will have to make do without full-back Drew Talbot however, who misses seven to ten days with a hamstring strain, Smith saying that he wanted to fill his berth on the left side with a left-footed player - suggesting a start for Dion Donohue or Derek Daly, the two left footers in Saturday's squad.
Peterborough have left-back troubles of their own with on-loan Leicester City player Callum Elder injured last time out against Blackpool, with regular in that position, Kgosi Ntlhe, also out injured.
However, another defender, Miles Addison, could feature after extending his initial month-long contract at London Road this week.
In the second successive season that the Posh and Spireites face off on Boxing Day, Saturday's hosts will be looking to gain revenge on the Eoin Doyle-inspired 3-2 Chesterfield win of 12 months previously.
Smith has been in charge for four games now, with the defensive side of the Spireites' game tightened considerably, just three goals conceded, though this has been at the expense of the attack, with Smith overseeing just one goal at the right end to date.
Ten games into incoming Posh manager Graham Westley's tenure and his latest outfit have scored seven wins already, blasting the side up the league and into the play-off positions at Christmas.
However, hope for the Spireites comes from the last two Posh games, finishing level with Shrewsbury Town at home before losing at Blackpool last weekend; two sides down the standings that United will have expected to continue their winning form against.
From the Dugout
Smith ran the rule of the Spireites' Boxing Day opponents, noting that his side will be in for a stern test in their aim to arrest their slump.
He said: "They've recently changed manager so they'll be strong under Graham Westley who has a reputation for working his players hard, that's something we need to come to terms with first.
"We've got to match their work rate and endeavour, and I don't think we'll have a problem doing that.
"We expect to go there and give a good account of ourselves but also come back with a result, because I think the league is that close that at any given time the top team can lose to the bottom team.
"We need to go there and be as confident as we can that we can make things change."
Despite the recent results, Smith says that he is sure that all his players are putting in all the effort required to get their form back on track.
He said: "We're working hard at trying to change things and I keep saying to the players that if you are working hard things will change eventually.
"We need to concentrate on doing the right things in training throughout the week and prepare properly.
"The players are giving everything they've got in matches, I can't single anyone out who's not giving 100%, and I'm sure eventually it will turn."