The former Man City player will have been left in no doubt about the scale of the task facing him as opponents Northampton did their own hopes of reaching the play-offs no harm what so ever with a convincing win.
The visitors took the lead on 22 minutes when slack marking by the Chester defence allowed Andy Kirk to latch on to a left-wing cross and poke the ball home.
Town had looked the side with greater urgency such was the importance of this game to their play-off ambitions, while Chester had little to play for other than pride.
Josh Low turned Carl Regan inside out and crossed to goalscorer Kirk who missed his kick in front of goal on 34 minutes.
A minute later Martin Smith was unlucky as his curling shot crept just past the post.
The visitors doubled their advantage two minutes after the restart as Kirk latched on to a headed knock on and turned inside Phil Bolland before sidefooting past keeper Chris MacKenzie.
The Chester keeper then denied David Rowson with a point-blank save and then a block on the rebound as the visitors continued to put pressure on their hosts.
With 20 minutes to go Chester almost gave themselves a lifeline, but Bolland's header from Ryan Lowe's free-kick came back off the post.
Kirk was unlucky not to complete his hat-trick when his solo run ended with his shot hitting the upright and a header from Scott McGleish also struck the post.
There was even time for Chester to miss a penalty when Ben Davies was fouled and then stepped up to send his effort well wide of the mark.