REPORT: Chesterfield 1-2 Accrington Stanley
The Spireites, who had Brad Barry sent off, have won just once this season and only three times in the 28 games since Caldwell took charge in January.
There were boos and calls for the manager’s head both during and after the game, which turned into an entertaining affair following a drab first half.
Chesterfield were well on top when Barry saw a 63rd minute red card for a needless and dangerous tackle deep in the Stanley half.
They went behind soon after and although Kristian Dennis equalised from the spot, a Mallik Wilks goal brought another defeat and heaped pressure on the under-fire boss.
The visitors started on the front foot and were presented with a golden chance when two Town players tackled each other on the edge of their own box and the ball was whipped in to Sean McConville who was denied by a fine Joe Anyon save.
It was a disjointed start from the hosts, particularly in possession as they struggled to create a noteworthy attack in the first 20 minutes - a Louis Reed through ball for a quickly closed down Kristian Dennis their best moment.
But they began to grow into the contest, seeing more of the ball albeit in areas that didn’t hurt the visitors.
Both Scott Wiseman and Zak Jules made surging runs forward with the ball down the sides before a ball pinged into the area was flicked well wide by Diego De Girolamo.
Anyon was called into action again with just over half an hour gone, a free-kick into the box headed goalwards by dangerman Billy Kee, the Town keeper tipping the ball onto his crossbar.
And in the final seconds of the half Jordan Flores gave the ball away to Kayden Jackson, fouled the striker to earn yellow and give a free-kick away in a decent attacking position for Accrington. McConville’s ball into the box was dealt with but his follow up shot drew another excellent one-handed save from Anyon.
Town made a bright start to the second half, probing in a good spell of possession high up the field, eventually leading to a De Girolamo shot that was well wide but drew cheers because it at least showed endeavour.
And the hosts seemed to take confidence from that, Flores seeing a dinked effort deflected over before a clever corner routine ended with Kristian Dennis’ shot saved from close range by Aaron Chapman.
The resurgence continued, an Andy Kellett cross from the left headed wide by Dennis before Louis Reed hammered high over the bar.
Seconds later the referee turned down strong penalty appeals from the home side, the ball clearly handled in the box but apparently not seen by Craig Hicks.
Robbie Weir sent a fierce drive just over the top and then came a sucker punch for Gary Caldwell - the already booked Brad Barry going into a challenge on Seamus Conneely with his studs up and earning a straight red.
The 10 men were lucky not to fall behind int he immediate aftermath of the sending off, Sam Hird’s last ditch tackle keeping Jackson at bay.
But on 69 minutes the almost inevitable goal arrived for the visitors, Kee afforded too much time and space at the back post, bringing down a cross and hammering it past Anyon.
Quite remarkably, the game swung back in the home side’s favour - replacement Chris O’Grady nodding on a high ball for Dennis who was pulled down in the box by Conneely - the man in red lucky not to see red, having already been booked.
This time Hicks pointed to the spot and Dennis blasted the spot-kick straight down the middle to level the game.
Parity was to last just five minutes, Accrington substitute Mallik Wilks sweeping a lovely strike into the far corner of the net from the edge of the box.
Try as they might, the Spireites were unable to trouble their visitors again and frustration showed, Hird given a yellow for dissent after another disputed decision from Hicks.
In the last seconds Janoi Donacien was booked for a foul on Gozie Ugwu and Anyon joined the attack for the resulting free-kick, which was easily cleared seconds before the final whistle.
Chesterfield: Anyon, Hird, Wiseman Jules (Ugwu 89), Kellett (Sinnott 72), Barry, Weir (O’Grady 72), Reed, Flores, Girolamo, Dennis. Subs: Jones, Maguire, McCourt, Briggs.
Accrington: Chapman, Donacien, Hughes, Rawson, Thorniley (Forbes 67), Nolan, Conneely, Clark, McConville, Kee, Jackson (Wilks 78). Subs: Browne, McLeod, Sykes, Johnson, Savin.
Goalscorers: Dennis 77; Kee 69, Wilks 82
Yellows: Barry 35, Flores 44, Reed 71, Hird 90; Conneely 41, McConville 78, Donacien 90
Red: Barry 63
Referee: Mr Craig Hicks. Assistants: Mr Richard Wild, Mr Mark Cuniffe.
Attendance: 4,487 (198)