The Blues exited the FA Cup, in North Yorkshire, as two goals from Dom Tear and a penalty from Richie Bennett earned Scarborough Athletic a place in the First Round.
Iwan Murray pulled a one back with a brilliant free-kick in added time, but it proved to just be a consolation as the hosts prevailed.
Charlie Caton had the first opportunity of the contest but his side-footed effort was comfortable for Ryan Whitley in the home goal.
Kurt Willoughby also had a sight of goal within the first 20 minutes but he snatched at his shot and it bounced wide.
Jonathan Greening’s men smashed the woodwork just after the half-hour mark through Bailey Gooda, whose half-volleyed strike bounced back off the bar, after it evaded Elyh Harrison’s outstretched palm.
Dom Tear put the hosts ahead in the 35th minute, after he bundled the ball past Harrison and over the line from close-range.
This came after great work from Kieran Weledji on the right wing, who looked dangerous throughout the first-half.
Scarborough doubled their lead just four minutes later, after referee Joe Moss pointed to the spot as Richie Bennett was taken down by Ben Pollock.
Bennett sent Harrison the wrong way and converted from 12 yards.
The Blues made a fast start in the second period, as Willoughby smashed a half-volley towards the near post but Whitley saved in acrobatic fashion.
Jack Bainbridge had the next Seals effort from long-range, but the Boro number one was equal to it again, as he palmed the ball away from danger.
Dom Tear grabbed the hosts’ third in the 65th minute as he raced in behind the Blues’ defence before he tucked a clever finish past Harrison.
Iwan Murray pulled one back in added time with a brilliant free-kick that flew past Whitley in the Scarborough goal.
The referee blew up immediately after though and our exit from the FA Cup was confirmed.
Calum McIntyre’s side will return to action next Saturday as we host a crucial clash with Scunthorpe United.
Match Report by Tom Bird.
CHESTER: Harrison, Hunter, Pollock (Murray 71′), Burke, Roberts, Bainbridge, Weeks, Glendon, Willoughby (Mottley-Henry 66′), Caton, Peers.
Subs not used: Mason, Hancox, Rosenblatt, Turner.
Scorers: Murray 90+3′
Attendance: 1803
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