Gloucester City 0
Chester FC 1
GLOUCESTER City's look set for a winter of discontent after dispiriting defeat at the hands of Chester FC.
Despite valiant defending the Tigers were again short of ideas in attack.
With more than 500 fans packing out the away end Chester started strongly, with Craig Curran drifting an early shot wide of Mike Green's goal.
City looked bright in midfield, with recalled winger Adam Mann shooting at Chester's Jon Danby after collecting a neat pass from Tom Webb.
Tom Hamblin's header at the back post was blocked off the line as the Tigers searched for a breakthrough.
But Chester were quick on the break, with former Cheltenham Town man Scott Brown pulling the strings. Matt Coupe blocked a Nathan Jarman pass on 16 minutes, making up for a poor clearance from Jack Harris.
Harris attempted to make amends at the other end moments later with a sublime overhead volley, nudged out for a corner by Antoni Sarcevic.
After 20 minutes Chester began to surge forward. Defender Mike Green miss-timed his header leaving Nathan Jarman free on goal, but Gloucester's other Mike Green saved well.
Jarman had two more shots stopped on the half hour mark, the first blocked by Hamblin, the second caught by Green.
Danny Williams hit the inside of the post on 37 minutes after collecting a loose ball and running through the City defence.
Keeper Green made another crucial save just before the break, stopping a stooping header from Brown.
Jarman continued to be the dangerman in the second half, heading the ball wide on 50 minutes.
City's talismanic midfielder Webb had a cross-shot saved on 54 minutes but it was no real threat to Danby.
Steve Davies' neat run through midfield was stopped on the edge of the box by Danny Williams on 57 minutes.
Jarman put Chester ahead on 65 minutes with a well weighted volley after keeper Green was distracted by Dave Hankin's mistimed bicycle kick.
Already booked, Hogg picked up his second yellow card for a seemingly innocuous tackle on Brown on 71 minutes and saw red for the third time this season.
Down to ten men, City did their best to get back in it, but still it was the visitors who pushed forward.
Curran's dipping shot was tipped over by Green on 78 minutes before Jarman fired into the side netting minutes later.
With no serious chances on goal in the second half manager Dave Mehew may be forced to ring the changes before Wednesday's visit of Colwyn Bay.
Gloucester City: M Green, M Green, A Mann ( M Harding 62) M Coupe, T Hamblin, T Webb, L Hogg, J Goddard (S Rawlings 73), D Edwards (W Morford 73) S Davies, J Harris. Subs not used: C Holland, N Mustoe
Chester: J Danby, W Baynes, D Williams, G Horan, D Collins, S Brown, T Gray (D Hankin 63) A Sarcevic, N Jarman (M Williams 89), C Curran (I Howard 84) , A Williams. Subs not used: P Linwood, S Clancy,
Ref: Craig Hicks
Star man: Mike Green (goalkeeper)