After the weekend's FA Cup exit at Derby County, the Spireites return to league action and welcome Crawley Town to the Proact Stadium.
The Sky Bet League 1 match will be the first ever visit of the Red Devils to Chesterfield, with the first ever game between the sides last November seeing a 1-1 draw at the Broadfield Stadium.
Since that match, the two teams' form has branched in two distinct directions, making the match all the more crucial for differing reasons for the competing sides.
Full back Daniel Jones was sent off in the corresponding away fixture, but is likely to start having broken back into the starting line-up in the past two matches.
Gary Roberts remains sidelined with a hamstring injury, but the Spireites squad otherwise emerged unscathed from the battle at the iPro Stadium on Saturday.
Crawley could give a Proact return to former Spireites striker Dean Morgan, who came off the bench to make his Reds debut in the weekend's 1-0 loss at Fleetwood Town, the striker has arrived at Crawley on loan from Woking until the end of the season.
However, the Red Devils will be without the injured quartet of goalkeeper Brian Jensen, defender Dean Leacock and midfielders Conor Henderson and Josh Simpson for the match.
Chesterfield's strong festive run has been challenged by back-to-back losses away at strong opposition in Swindon Town and then Derby County, but with cup distractions now out of the way the sole focus will switch to the hunt for the League 1 playoffs.
The Spireites have won their last three home matches and a fourth consecutive triumph would move them up into fifth spot in the division.
Tuesday's opponents, however, are concerned only with survival this season. Propping up League 1 and five points off safety, the Reds have gone 14 games and over three months since last tasting victory.
That said, the recent draw with MK Dons, a game the West Sussex side had lead 2-0 at one point, showed that Crawley can be a match for even the best in the division on their day.
From the Dugout
Speaking ahead of the game, Spireites manager Paul Cook stressed that of the upcoming run of mainly home fixtures, the first one against Crawley was particularly crucial.
"I think tomorrow's game's the most important," said Cook. "When you look at games we've got coming up like Preston and Leyton Orient, those games normally look after themselves, but tomorrow's the big one.
"Tomorrow's a massive game for the club because there's a lot of teams who can suffer cup hangovers and one of the problems for players and supporters is the euphoria you go and build up for the game on Saturday, the atmosphere and the feeling around the ground, and then you come to tomorrow's game.
"People will be turning up maybe expecting us to win, they don't get themselves up for it. The supporters have carried us at some points this season and tomorrow we're really going to need them. If we are flat, they can give us that other ten percent."
With their higher league standing, Chesterfield will be heavily-fancied for the Proact match up, but Cook was keen to point out just how narrow the margin is between teams in the division.
He said: "There's no such thing a s a clear favourite in this league. The gaps between the top teams and the bottom teams is very small now.
"You only need two or three injuries to put yourself on the backfoot. Our first aim is to maintain our status in the league and then you go from there.
"We go fifth in League 1 if we win tomorrow night. If someone had offered us that at the start of the season we'd have we'd have bitten their hands off. We'd have said what a big game this is on Tuesday night, and that's what it is.
Spireites supporters unable to make the game tonight can follow full match commentary live on Spireites Player. Elsewhere there is minute-by-minute coverage on Twitter and score updates on Facebook.