The Glovers head to Derbyshire looking to get off the mark away from home.
Having come away from their first four trips on the road empty handed, Town are looking to collect their first away league points of the campaign.
Darren Way's side comfortably beat Exeter City 3-1 at St James Park in the Checkatrade Trophy in August, so will be looking to correlate that performance into Sky Bet League Two on Tuesday night.
Having faced lowly Port Vale on Saturday and shared the spoils, Yeovil will take on a Chesterfield side who currently sit 23rd in the table.
A 2-1 defeat at home to Accrington Stanley two weekends ago saw manager Gary Caldwell sacked, seeing Guy Branston take caretaker charge at the Proact Stadium.
The switch didn't see an immediate response, as the Spireties lost 1-0 to promotion chasing Luton Town on Saturday.
Striker Kristian Dennis, plucked from non-league last summer, is the club's top scorer with four goals, while experienced strike partner Chris O'Grady has netted just once so far.
Chesterfield boast just one former Glover in striker Gozie Ugwu, who has spent time at Huish Park across two spells.
The Glovers are undefeated in their last four trips to the Proact Stadium.
Playing out a 0-0 draw in the last meeting between the two sides in 2014, Town's one victory in Derbyshire came in 2006, with an Arron Davies hat-trick confirming a 3-0 win.
Yeovil's last defeat at Chesterfield came 67 years ago, in a 3-1 FA Cup Third Round loss.
Tuesday's meeting will be the first match between the two sides since April 2015.
David Coote will be the man in the middle at Chesterfield.
It will the first time Mr. Coote has officiated a match involving the Glovers since October 2012, when he oversaw a 3-1 Town win at Shrewsbury.
Taking charge of 39 matches in the 2016/17 season, Mr. Coote awarded 127 yellow and seven red cards.
On Tuesday, Mr. Coote will be assisted by Nick Hopton and Adam Matthews, with Karl Evans acting as fourth official.
If you’re unable to attend the game, live audio commentary is available via the iFollow Glovers service, with the monthly and season subscriptions offering full-match replays from Sunday.
A full match report will follow on YTFC.net at full-time with post-match reaction from the manager and a member of the playing staff following soon after.
Fans can still buy tickets in advance in person at the ticket office or by phone on 01935 847888. Tickets are also available on the day of the game. Prices can be found here.