A disappointing display by the Blues saw Tranmere ease to victory at Prenton Park.
First half goals by Liam Hogan and James Norwood secured victory for Rovers.
The game - backed by an incredible following from both sides - started in cagey fashion, until the deadlock was broken on five minutes.
A Tranmere corner was not cleared by the Blues - and Liam Hogan headed home with Jon Worsnop stranded off his line.
The time had doubled by the time the Whites should have doubled their lead.
A quick goal kick from Scott Davies completely caught out the Chester backline, and - with plenty of time and space - Norwood only managed to hook his shot straight at Worsnop.
The Blues slowly did work their way back into the half as it progressed - with Johnny Hunt being the first to test Scott Davies.
However, the threat on the counter attack of Gary Brabin's side was always a worry - as Matt Hill blasted a shot over for the hosts midway through the first half.
Ross Hannah would then sting the palms of Davies - before the hosts doubled their lead.
Norwood picked up the ball around the halfway line, and drove on past the defence before slotting home past Worsnop.
Even into the second half, Steve Burr's side struggled to get back into the game - with Rooney forcing Davies into two comfortable saves.
Nevertheless, Chester were handed a lifeline with just a quarter of an hour remaining when a Tranmere defender handled a Sam Hughes header inside the area.
But, the ever-reliable John Rooney saw his spot kick saved brilliantly by Scott Davies.
The hosts continued to push for a third at the other end - Worsnop saving Norwood's effort with his legs when the forward was in behind the defence once again.
Ryan Higgins was the next to find himself a chance, but couldn't control his volley at the back post as it flew over the bar.
Substitute Craig Hobson headed wide in stoppage time - a chance which concluded a bleak afternoon in Birkenhead.
Tranmere: Davies, Sutton, Jennings, Hogan, Harris, Norwood (Margetts 90+4), Ihekwe, Mangan (Maynard 86), Hill, Mekki, Dawson (Jackson 79).
Subs Not Used: Turner, Ridehalgh.
Booked: Dawson, Ihekwe
Chester: Worsnop, Kay, Heneghan, Sharps, Hunt, Higgins, Rooney, Shaw, Mahon (Hughes 46), O'Hanlon (Richards 65), Hannah (Hobson 70).
Subs Not Used: Forth, Chapell.
Booked: Hughes, Rooney, Kay
Scorers: Hogan 5, Norwood 37.
Attendance: 7,433 (1,526 away)
Referee: Mr Simon Bennett