Coventry City slipped to a 2-1 defeat by Crewe Alexandra at Gresty Road, in a game that saw the Sky Blues end the match with ten men.
Goals from Febian Brandy and George Cooper gave the Railwaymen a two goal lead at half time. An own goal gave City a chance of a comeback, but it was not enough to prevent City losing for the fourth time in five league games.
Manager Steven Pressley made four changes to the side that beat Exeter in the Johnstone's Paint Trophy, with Ryan Allsop, Danny Pugh, Jim O'Brien and Seb Hines all coming into the side to replace Lee Burge, Ryan Haynes, Andy Webster and Mohamed Coulibaly respectively.
Despite being in a poor run of form the hosts started the game brightly, enjoying large spells of possession, as City looked to get a foothold.
After four minutes the Alex had the first chance of the match. Matt Tootle curled a free kick into the area, and George Ray lifted the ball onto the roof of the net.
The tempo from both teams was high in the opening stages, with some real blood and thunder tackles being put in all around the pitch. City had their first effort on target after ten minutes, John Fleck's long range drive palmed around the post by Ben Garratt.
The Sky Blues started to get into the game more and Josh Mcquoid had an effort comfortably saved a couple of minutes later, his shot straight at the keeper.
It was becoming end to end stuff and the Railwaymen had appeals for a penalty turned away when Brandy went on a mazy dribble and went down from a Jack Finch challenge.
Allsop had to make his first save of the match in the 18th minute, getting down smartly to parry away a header from Ray.
Hines was then desperately unlucky not to open the scoring a minute later, his header going straight into the arms of Garratt.
The game was becoming a fractious affair, with a succession of fouls constantly stopping the flow of play.
Just after the midway point of the first half the Alex took the lead. Brandy was released by a through ball and showed composure to shrug off the challenge of Danny Pugh and slot it through the legs of Allsop.
City tried to pick up the pace but their task was made even harder when the Railwaymen doubled their lead after 33 minutes.
Cooper ran at the Sky Blue defence and was brought down just outside the area. He took the resulting free kick himself and put it right in the top corner, giving Allsop no chance.
City were facing an uphill task, but Simeon Jackson almost pulled a goal back immediately, firing just wide from a tight angle.
The Sky Blues were enjoying much of the ball in Crewe's half, but were unable to create any clear cut chances, and went into the break two goals down.
The second half started brighter for City. and they nearly scored after just a few seconds. Aaron Philips had a shot blocked on the goal line, and Josh McQuoid was unlucky not to turn the loose ball in.
The Sky Blues did get a goal back three minutes into the second half. Danny Pugh's free kick was headed into his own net by Anthony Grant.
All of a sudden City's tails were up and the travelling Sky Blue Army were creating a tremendous atmosphere inside Gresty Road. Fleck fired just wide from 25 yards, and the momentum was all with the visitors.
Some fierce tackles were flying in and the game was becoming decidedly edgy, with both teams knowing that a fourth goal would be crucial either way.
The Sky Blues then made a change to help their search for an equaliser, the more attacking minded Coulibaly coming on for Conor Thomas.
With twenty minutes to go the Sky Blues changed formation and brought on Shaun Miller for Seb Hines as they continued their push for a second goal.
A trio of successive corners provided opportunities for City, but some stout defending from the Alex kept the Sky Blues at bay.
Any hopes of an equaliser were dealt a major blow when Jack Finch was given a red card after a second bookable offence eight minutes from time.
With two minutes of normal time remaining Coulibaly struck a fizzing shot wide of the far post, as chances were becoming more and more sparse.
Five minutes of additional time was added by the fourth official, but the Railwaymen held on with their extra man advantage, and condemned City to defeat.
: 5058 (1084 Away)
Coventry City: Allsop, Willis ©, Pugh, Thomas (Coulibaly 64'), Fleck, McQuoid, O'Brien (Maddison 79'), Jackson, Phillips, Hines (Miller 70'), Finch
Subs: Richards (GK), Webster, Tudgay, Haynes,
Crewe Alexandra: Garratt, Toole ©, Ray, Dugdale, Turton, Inman, Cooper, Leigh, Brandy (Atkinson 84'), Tate, Grant
Subs: Shearer (GK), Guthrie, Oliver, Saunders, Nolan, Ness