A busy January transfer window saw four players arrive and four depart as new boss Gary Caldwell looked to put his own stamp on the first team.
Caldwell welcomed Birmingham City’s Reece Brown and QPR defender Osman Kakay on loan until April 30. The Spireites later added David Faupala of Manchester City and Preston midfielder Liam Grimshaw, for the rest of the season.
The new arrivals meant players must depart, club captain Gary Liddle left for Carlisle while attacking midfielder Jay O’Shea went to Sheffield United earlier in the window.
They were then joined through the door on deadline day by Liam O’Neil, who was brought by Cambridge United, and Gboly Ariyibi, who was prized away by Nottingham Forest.
The experienced four made over 330 Chesterfield appearances between them and here we take a look at their greatest moments in the blue and white.
Jay O’Shea - Promotion Winning Brace
There will be little doubt amongst supporters as to O’Shea’s finest moment for Chesterfield. Signed on a free transfer from MK Dons, the attacking midfielder made over 170 appearances for the Spireites over four years.
The Irishman notched an impressive 36 goals during his time at the Proact, but his promotion confirming brace against Burton Albion will live long in the memory of Chesterfield fans.
Paul Cook’s men knew a win would secure them automatic promotion and were well on their way to victory when O’Shea flicked a Ritchie Humphreys' cross past Burton ‘keeper Dean Lyness.
O’Shea then confirmed promotion with a second, knocking in the rebound after Lyness had saved Eoin Doyle’s original effort.
Gary Liddle - Being given the captaincy
The former Bradford City midfielder joined the Spireites in January 2016 with over 400 appearances to his name. Signed to fill the void left by captain Sam Morsy, who had just departed for Wigan Athletic.
The 30-year-old was awarded the captaincy shortly before his first match and immediately announced his pride on taking the role.
He told the club website: “I am delighted, I found out before the game. The manager called me into his office and said he’d like a different voice out there.”
He may not have had the greatest start as captain, succumbing to defeat at the Proact against Peterborough, but it will remain a proud moment for the now Carlisle player.
Liam O’Neil - Match winning goal against Bolton
The Cambridge-bound midfielder scored a second goal in as many games as the Spireites secured a famous victory against promotion favourites Bolton Wanderers.
Having spent the majority of his Spireites career at full-back, the Englishman was given a chance to stake a claim in his natural position and impressed with a series of dominating performances.
The culmination of which came as Chesterfield beat Bolton 1-0 at the Proact earlier in the season, the 23-year-old knocking in a cross from Ariyibi to secure victory.
Gboly Ariyibi - First ever professional goals
The American winger may have blown hot and cold during his spell with the Spireites but his dazzling displays and tricky feet wowed supporters on a number of occasions.
Having rejected a deal with Premier League Burnley to join the Spireites, the winger set about making his mark at the Proact, quickly becoming a fan favourite with his direct running style.
Having impressed in his short time at Chesterfield so far, the American-born winger secured a further two-years with the Spireites on March 11, 2015 and just a few days later celebrated it by scoring his first ever professional goal.
Although just 20-years-old, Ariyibi had already played for three different clubs, struggling to break into the first team at both Southampton and Leeds but found a home at the Proact.
The only thing missing from his performances for Chesterfield had been goals, but this changed when he smashed home a strike against Coventry City, having been played through by Gary Roberts. The match would finish 2-3 to the Sky Blues, but Ariyibi was off the mark