Southend United lost 2-1 to League 1 side Walsall in the first round of the Capital One Cup on Tuesday night.
Mal Benning gave the visitors a first-half lead, finishing from close range after an excellent cross from left-back Andy Taylor.
Ryan Leonard produced an early contender for goal of the season with a stunning free-kick from 25-yards to level midway through the second-half.
Kieron Morris then won it for the League 1 side with just a couple of minutes remaining, to secure their progress to the second round.
Phil Brown made seven changes for the cup tie, with only Shaq Coulthirst, Luke Prosser, Ryan Leonard and Ben Coker, who captained Blues in the absence of John White, keeping their place.
There was a debut for Mads Ibenfeldt, while David Worrall made his first start for the club having come off the bench against Accrington Stanley. The changes also gave Brown the opportunity to test a 3-4-1-2 formation, with Jack Payne in behind Coulthirst and Lee Barnard.
It was Blues’ stand-in skipper Coker who had the first chance of the game. Payne, making only his third start in a Blues shirt, fizzed it out wide to Coker, but he fired an effort over the bar after going on his own.
Blues had done well to adapt to the formation and stop Walsall from playing, but with 25 minutes gone, the League 1 side took the lead.
Benning controlled a long goal kick from Richard O’Donnell beautifully and laid it out wide to Taylor. The left-back’s cross was inch perfect for Benning who tapped past Paul Smith in Blues’ goal.
Brown’s side looked for an instant response but were halted when Will Atkinson had to go off having picked up a knock to the head in an earlier challenge. Conor Clifford was the man to replace him.
It was fellow midfielder Payne who went closest to restoring parity for Blues with a great strike from just inside the box. Unfortunately for Blues, O’Donnell was equal to the effort.
Clifford then found Barnard with a clever through ball, but the striker’s effort was again well kept out by O’Donnell who dived at his feet.
Moments before half-time, Blues were aggrieved Walsall had not been reduced to ten men as Paul Downing fouled Barnard as he looked to get a shot off.
The referee gave a yellow card, and a free-kick inches outside the box, rather than a penalty and Payne’s effort from the dead ball was blocked by the wall.
Despite trailing, Blues were playing some good football and went close to levelling with ten minutes gone of the second half. Adam Thompson met Coker’s corner, but the defender’s bullet header went narrowly wide.
Playing just behind the front two, Payne was getting some joy in attacking areas, and almost drew Blues level on the hour mark.
Clifford’s adventurous run ended with a good defensive block, but the ball broke kindly for Payne. He kept the strike low, but O’Donnell got down well to make the save.
Payne then turned provider as he played a lovely pass into the path of Coulthirst, but the striker dragged his effort just wide of the target.
Blues finally got the reward their pressure deserved with 67 minutes on the clock. Payne was fouled 25-yards out and Coker rolled the ball a couple of yards into the path of Leonard who smashed it past O’Donnell.
Walsall’s ‘keeper had no chance with Leonard’s strike but he did superbly to keep the scores level moments later.
Prosser got a big deflection of Thompson’s volley that took it towards goal, but O’Donnell did brilliantly to palm the ball away.
Blues continued to press but were undone with a couple of minutes remaining. Morris picked the ball up, turned, and hit a venomous strike that beat Smith.
Brown’s side pushed for another equaliser but for the second season running, they were beaten by a single goal against higher opposition in the first round of the Capital One Cup.
Blues: P. Smith; Thompson, Ibenfeldt, Prosser; Worrall (Weston), Leonard, Atkinson (Clifford), Coker; Payne (Hurst); Barnard, Coulthirst.
Subs: Bentley, White, Corr, Bolger