The Spireites came from behind at Barrow on Tuesday night and took the lead but ultimately lost 3-2 - their first defeat of the season.
Chesterfield took a 2-1 lead on 50 when Will Evans headed in a Zavon Hines free-kick but the game turned two minutes later when Jerome Binnom-Williams was red-carded and Barrow took advantage of the extra man. Tyler Smith, borrowed from the Blades, scored on 68 and again on 71 to turn the game round.
Jack Hindle had opened the scoring before Hines quickly equalised and four minutes from time, home sub Steve Jennings was dismissed to briefly level the numbers up, but the Spireites, despite having chances, were unable to regain parity.
Birthday boy Martin Allen made one change to the starting XI. Gozie Ugwu was absent and replaced by Sam Wedgbury, who was making his first Spireites start, though his match was short-lived after he picked up an injury.
Laurence Maguire returned to the bench alongside keeper Joe Anyon, named in the matchday squad for the first time this season.
Former Spireites favourite Ian Evatt included ex-Chesterfield team-mate Josh Kay in the Bluebirds side for the first clash between these clubs since 1967. Evatt has performed major surgery at Holker Street having brought in 16 new players since his arrival in the summer.
Wearing their new orange change kit for the first time this season, the Spireites were under pressure early on as Kyle Jameson blasted over following a Dan Jones monster throw. Marc-Antoine Fortune carved out an opening for himself but Andrew Firth saved well.
Hindle fired the hosts ahead on seven when he blasted home from ten yards from Smith's right-sided cross, but that lead lasted just seven minutes; a right-sided free-kick was worked to the left and Binnom-Williams crossed in for Hines to glance home a header for his second goal of the season.
Wedgbury was stretchered off with what looked a nasty injury, not caused by contact, George Smith coming on for a birthday treat, moving to left midfield allowing Charlie Carter to switch to the right.
Chesterfield's back line began to deal with Barrow's nippy trio of strikers and chances started to be less frequent though the hosts created three openings in the latter stages of the first half. Jones headed high, Jason Taylor forced a deflection for a corner just before he had to be subbed and Jameson's shot required a fingertip save from Shwan Jalal, another birthday boy.
The visitors started the second half in the best possible manner with Evans' glancing header matching Hines' earlier effort, handing the Spireites the lead for the first time but the red card for Binnom-Williams, for a foul on Nathan Waterston, changed the balance of the game.
Just as Chesterfield looked to have begun to settle with their numerical disadvantage, Barrow's Smith calmly slotted the leveller and then headed in at the far post from John Rooney's deep cross from the right.
Rooney had a shot tipped onto the bar by Jalal and that save was matched by Firth when Carter's free-kick was pushed wide at full stretch.
Jennings, on his debut, was dismissed late on to level the numbers but Carter couldn't quite level the scores when he was put through on the edge of the six.
Barrow: Firth, Brown (Barthram 60), Granite, Jameson, Jones, Kay (Burgess 66), Taylor (Jennings 45+5), Rooney, Hindle, Smith, Waterston. Subs (not used): Correia, Molyneux.
Goals: Hindle 7, Smith 68, 71
Chesterfield: Jalal, Talbot, Evans, Nelson, Binnom-Williams, Wedgbury (Smith 29), Weir, Weston, Carter, Hines (Shaw 61), Fortune (Maguire 54). Subs (not used): Anyon, Muggleton.
Goals: Hines 14, Evans 50
Ref: Joe Johnson
Bookings: Weir, Evans (Chesterfield), Granite (Barrow)
Dismissals: Binnom-Williams (Chesterfield 52), Jennings (Barrow 86)
Attendance: 1,701 (306 from Chesterfield)