A sublime goal from Francis Tierney proved the difference as Doncaster Rovers once again got the better of Chester City.
Following up on last season's play-off defeat of the conference outfit, Rovers just edged it to claim a place in the second round of the LDV Vans Trophy.
The visitors started brightly and should have been in front as Michael McIndoe wasted two glorious chances in quick succession.
Chester produced their one real bright moment in first half stoppage time as Ian Foster whipped in a cross from the left flank but Kevin Rapley headed wide.
The deadlock was broken on 62 minutes as Tierney picked up the ball on the right hand edge of the box and curled a left-footed effort into the top corner giving Blues keeper Wayne Brown no chance.
In the closing stages former Rovers player Kevin McIntyre had to be on his toes to deny a header from Mark Albrighton that was flying into the net.
Chester's misery was compounded as late substitute Peter Dogun was given a straight red card for a two-footed lunge on Jon Maloney.