Chesterfield finished seventh in the final stands, boasting 74 points from their 44 matches, while Halifax were fourth behind Solihull Moors, 10 points above their opponents in this contest.
Halifax won 25, drew nine and lost 10 of their 44 matches during the regular National League campaign to collect 84 points, which left them in fourth spot in the table, three points behind third-placed Solihull Moors, who are already in the semi-finals of the playoffs alongside Wrexham.
The Shaymen have spent the last five seasons in the National League following their promotion from National League North, and it would be some story if they could navigate their way through the playoffs to secure a position in the Football League.
Pete Wild's side will enter this contest off the back of a 2-0 defeat at Stockport County on May 15, which followed a 1-1 draw with Aldershot Town in their last home fixture.
The fact that Halifax picked up 10 more points than Chesterfield should mean that their confidence is high heading into this quarter-final, while they recorded a 2-0 victory when the two teams locked horns at the Shay in the middle of last month.
Chesterfield, meanwhile, have spent the last four seasons in the National League following their relegation from the fourth tier at the end of 2017-18.
The Spireites only just managed to sneak into the playoff spots this season, picking up 74 points from their 44 matches, which left them one point clear of eight-place Dagenham & Redbridge.
Chesterfield will not enter this match in the best of form, meanwhile, having picked up just one point from their final four league matches of the season, which was a goalless draw at home to Woking last weekend.
Indeed, Paul Cook's side lost to Bromley, Stockport County and Torquay United in the latter stages of the regular season, with their last victory coming a month ago at home to Dover Athletic.
Chesterfield actually had the fifth-best away record in the 2021-22 National League, picking up 34 points from 22 matches, but they will be taking on a Halifax outfit with the strongest home record last term, having collected 53 points from their 22 games in front of their own fans.
Jack Senior, Martin Woods, and Niall Maher all came into the Halifax side for the clash with Stockport last time out, but the trio are under threat from Javid Swaby-Neavin, Kieran Green, and Harvey Gilmour here.
Woods is a major doubt with the problem that he picked up last weekend, and it seems likely that head coach Wild will make alterations for the playoff affair.
Billy Waters and Jordan Slew have 28 league goals between them this season, and the pair are set to continue in the final third of the field, with Matthew Warburton, who has netted 13 times in the league this term, operating in a deeper position.
Chesterfield, meanwhile, have no fresh injury concerns ahead of the contest, and there are not expected to be any real surprises in their starting lineup on Tuesday night.
Kabongo Tshimanga is the team's leading goalscorer this season with 24 in the National League, but the 24-year-old is still out through injury, so Cook has decisions to make in attack.
Halifax Town possible starting lineup:
Johnson; Swaby-Neavin, Bird, Debrah; Warren, Gilmour, Warburton, Spence, Senior; Waters, Slew
Chesterfield possible starting lineup:
Loach; Williams, Grimes, Whittle; King, Kellermann, Mandeville, Weston, Rowe; Khan, Asante
We say: Halifax Town 2-1 Chesterfield
This has all of the makings of a brilliant game of football, but Chesterfield's form ahead of this match is a real concern. Halifax have so much talent in the final third of the field, meanwhile, and we are expecting Wild's side to advance courtesy of a narrow success on Tuesday night.
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