Having triumphed in the first round against Northampton Town, Chesterfield will be looking to make the next stage of the Cup for their second consecutive season. They will be hunting for an upset against a Wimbledon side just one division above them, who themselves have reached five of the last six third rounds.
Match preview
Johnnie Jackson's Wimbledon will be reaching the halfway point of the season quietly optimistic of their progress.
After his predecessor Mark Robinson helped relegate the Dons last season with a dismal league performance, Jackson was brought in on a two-year contract to bring them back to League One, where they had been since 2016.
Jackson's team may only lie in 13th place in League Two, but their form has picked up significantly in recent weeks - three wins and just one defeat in their last seven games shows a clear boost, as does a 10-game unbeaten run in all competitions.
The Dons had to take National League South side Weymouth to a replay in the first round to reach this stage. After being limited to a 1-1 draw at the start of the month, they eventually overcame the Dorset minnows 3-1 at Plough Lane.
Weymouth could have taken the lead against Wimbledon if Tom Blair managed to turn in a gilt-edged chance from eight yards out in the first half. Weymouth captain Xander McBurnie hit the crossbar from 25 yards out as well, in what would have been one of the goals of the tournament thus far.
Luckily, quick thinking on a deep free kick saw Wimbledon's golden boy Ayoub Assal drive unmarked on the left flank into the Weymouth box, delicately stroking the ball past the keeper in a wonderful solo effort to make it 1-0.
Thirteen minutes later, Assal was involved again, dinking the ball to the head of Harry Pell, who spooned it up to substitute Ethan Chislett at the back post to make it 2-0. Weymouth barely managed to get the ball back when Chislett grabbed his second, finishing an excellent team goal a few minutes later, putting the game out of sight and putting the Dons into the second round.
Assal has absolutely blossomed this season under the coaching of Jackson, leading counter-attacks on the left for the Dons and scoring seven goals in midfield in his last nine appearances. Former Colchester man Pell dominates the midfield, a true box-to-box player, and Chesterfield will have to be on guard to stop the 31-year-old.
The optimism of Wimbledon's performances is, of course, levelled by the reality that they are still mid-table and outside of the playoff positions. The same cannot be said of their counterparts Chesterfield this weekend, who go into this match in fine form this season.
Paul Cook's men sit in third place in the National League, winning four of their last five fixtures, and their last defeat coming at the start of October with a 2-1 defeat away to mid-table side Eastleigh. The Spireites seem realistically set for their second consecutive playoff battle, and may even fancy themselves for automatic promotion.
Chesterfield triumphed in the Cup against League Two side Northampton Town at the start of the month, when 21-year-old forward Armando Dobra netted a deflected shot from outside the box in what proved to be the winner in the 14th minute. Northampton wasted golden chances to equalise at the Technique Stadium, with Kieron Bowie missing a key chance at the end to take the Spireites to a replay.
Chesterfield, of course, held on - and holding on to one-goal leads is more or less part and parcel with their style of play - unlike the gallivanting Wrexham and Notts County, Cook's team have a limited goal difference, winning many games by small margins.
They will need to retain their defensive solidity away from home this time, but if this season has proven anything for Chesterfield, it is that they are more than capable of shutting up shop when necessary.
AFC Wimbledon FA Cup form:
D
W
AFC Wimbledon form (all competitions):
D
W
D
W
W
W
Chesterfield FA Cup form:
W
Chesterfield form (all competitions):
D
W
W
W
W
W
Team News
Wimbledon will be looking to recall Brentford loanee Nathan Young-Coombes to the squad against Chesterfield. The 19-year-old forward had been in fine form for the Dons before he was stricken with a knee injury in mid-September.
Lee Brown, Will Nightingale, Paul Osew and Chris Gunter will certainly miss Saturday's cup tie. Huddersfield Town loanee Kyle Hudlin was stopped by his parent club from playing in the Weymouth tie, and is a doubt for this match.
Chesterfield may be looking to see a surprisingly early return to fitness for midfielder Ollie Banks.
Having been out for over a month with a hamstring injury, Banks had been set to be sidelined until December, but assistant manager Danny Webb has talked up Banks's fitness this week, and we may see him return to the Chesterfield squad.
Webb also confirmed Dutch striker Akwasi Asante will be in the squad for the Spireites; Asante has missed the last month alongside Banks with a hamstring injury, but has returned to training this week.
Lucas Covolan (ankle) will remain out, and Manny Oyeleke (knee) will not return to the side until the New Year.
AFC Wimbledon possible starting lineup:
Tzanev; Ogundere, Kalamabyi, Towler, Currie; Woodyard, Pell, Maghoma; Chislett, Assal, Davison
Chesterfield possible starting lineup:
Fitzsimons; King, Grimes, Williams, Clements; Jones, Oldaker, Whelan; Mandeville, Dobra, Quigley
We say: AFC Wimbledon 1-1 Chesterfield
Wimbledon have a lot of quality in their squad, and the likes of Pell, Assal and Chislett represent the cutting edge that Jackson has at his disposal.
However, Cook is an experienced coach with a lot of confidence in his side's ability to grind out results. Wimbledon's counter-attacking thrust will likely be anticipated by Chesterfield, and Cook's approach will likely cancel out both sides' ability to gain a definitive result at Plough Lane.