Blues suffer FA Cup heartbreak at the hands of Chester
Blues bowed out of the FA Cup First round after suffering defeat to non-league Chester at Roots Hall.
Early strikes in the first and second half sealed Chester's passage, with Blues' goal coming from Barry Corr mid-way through the first half.
Phil Brown named an unchanged starting XI from the side that defeated Mansfield Town seven days earlier, and Conor Clifford returned to the bench after missing out on the squad for the trip to Nottinghamshire.
Things began disastrously for Blues, with Ben Henaghan heading home from Peter Winn's free kick on the right-hand side after only five minutes.
Blues responded well to the early setback, with Corr going close with two headed attempts in quick succession – one going just past the post, the other into the gloves of goalkeeper Jon Worsnopp.
After 13 minutes, a good run from Jerome Williams saw the left back's cross reach David Worrall, who fired across the ball and seeing his shot go past the post.
Five minutes later and a rasping effort from Myles Weston flew inches past Worsnopp's left-hand post as Blues searched for a quick equaliser.
At the other end, John Rooney hit straight at Bentley before Craig Hobson really tested the Southend 'keeper just moments later with a low, curling effort.
On the half an hour mark, Blues were awarded a penalty after John White was pulled back by Rooney in the box. Up stepped Corr, who sent Worsnopp the wrong way from the spot and get Blues back on level terms.
After the break, Blues came straight out of the traps, and after a minute of the game resuming, Jakub Sokolik fired just over the bar on the half-volley after a Worrall corner wasn't cleared correctly.
However, on 51 minutes, Chester re-took the lead through Craig Mahon. The winger cut in from the right-hand side before firing past Bentley from the edge of the box.
Just before the hour mark, captain White had a great opportunity to get Blues back on level terms. After cutting in well from the right, the skipper saw his strike go just past the post.
Moments later, Worrall's diving header forced a terrific reaction save from Worsnopp after a superb cross from Leonard.
On the hour mark, Brown made a double substitution, with Kevan Hurst replacing Worrall, and Shaq Coulthirst coming on for Gary Deegan.
Blues kept having a lot of the ball without garnering any clear cut opportunities.
With 15 minutes of the game remaining, substitute Coulthirst fired over Worsnopp's goal from a narrow angle, as Blues through more men forward looking for the equaliser.
With seven minutes remaining, Jack Payne – who had come on for Corr with 20 minutes left – played a great one-two with Weston but curled his strike the wrong side of the post.
Payne drove an effort well over the bar from long range in a last ditch attempt to snatch something from the game.
However, that was to prove the last real opportunity for both sides as Blues made their exit from the competition.
Blues: Bentley; White (c), Sokolik, Prosser, Williams; Worrall (Hurst, 60), Deegan (Coulthirst, 60), Leonard, Timlin; Corr (Payne, 70), Weston.
Subs: T. Smith, Atkinson, Bolger, Clifford