George Baker-Moran’s second-half penalty was all that separated the teams, and Danny Heath’s sides could look back ruefully after hitting the woodwork on two occasions. Cameron Brown struck the right-hand post at the end of the first half, whilst Bobby Unwin curled a free-kick against the opposite upright in the final seconds of the match.

Youth team coach Heath made two changes from the starting eleven that had defeated AFC Wimbledon in their previous fixture, with Ergis Shala and Damarey Anyadike restored to the side in place of Jimmy Wallace and Freddy Eastwood.

Goalkeeper Callum Taylor had earned the plaudits of Heath following that win over the Dons, but it was his counterpart in the Gillingham goal, Mac Chilsolm, that was called into action first in just the second minute when he was called upon to save from Unwin, who had cut inside from the right flank to shoot with his favoured left foot.

Taylor was shielded by defender Tommy Davis shortly afterwards as the central defender tracked the run of Baker-Moran before making a strong challenge in the penalty area. However, Taylor did well in the 16th minute to tip Harry Laing’s corner off the head of Ronnie Nelson at the far post, and he then denied Harvey Lintott after he had met another Laing flag-kick.

Southend were not on the back foot for long, and Unwin set up Brown in the 19th minute. The midfielder held off Josh Chambers, but he slipped as he delivered his shot and it flew wide of the right-hand post. Unwin then stung the palms of Chilsolm with a fierce drive midway through the first half before the winger side-footed wide when well-positioned to convert Anyadike’s right-wing cross.

Unwin had another opportunity to open the scoring on the half-hour mark after schoolboy forward Adetayo Adeooja had won the ball on the left-hand side. He set up Unwin, who lost his footing and fired wide, before Adeooja smashed narrowly over himself from 25 yards out after holding off the attention of Matt Baker.

The first half ended with chances at either end. In the 42nd minute, good build-up play by Ahmet Biler and Unwin led to Brown curling against the frame of the goal from 25 yards out. Play then switched immediately into the Blues penalty area, where Taylor pulled off a superb save by flinging himself to his right to turn Baker-Moran’s glancing header around the post.

Adeooja directed a shot over from an Unwin pass early in the second period, but Blues were set-back when Gillingham took the lead in the 50th minute. Davis was adjudged to have fouled Baker-Moran as he entered the penalty area, and the forward stepped up to send Taylor the wrong way from the spot.

Southend could have responded within two minutes when Unwin burst into the penalty area and drilled the ball across the six-yard box. Anyadike slid in at the back post, but he couldn’t get a toe to the ball to divert it into the net.

Eastwood was brought on for Brown just before the hour mark as Blues tried to mix up their attacking options and, although Laing fired over for the visitors, Southend had chances to equalise soon afterwards. Biler exchanged passes with Unwin before forcing Chilsolm to parry his shot out, and Oli Coker then saw his follow-up charged down.

Biler’s ferocious strike was charged down on the edge of the penalty area midway through the second half, and Eastwood almost managed to thread the ball through to Adeooja in the 72nd minute with a fine reverse pass. Chilsolm was off his goal-line quickly to grab the ball at the striker’s feet.

Coker then set Anyadike away with a quickly-taken free-kick three minutes later, but despite initially catching the Gillingham defence unawares, they recovered to cut out the cross. Toby Bancroft dragged an effort wide for the Gills, but Southend piled on the pressure as the match entered the closing stages.

Chilsolm was perhaps fortunate not to be dismissed when he brought down Adeooja in the 90th minute as the striker advanced on goal. The custodian was then lucky when he was beaten by Unwin’s resultant free-kick, only to see it bounce back off the post.

Even in the fourth minute of stoppage time Blues almost managed to steal a leveller, but Unwin’s rollicking run was ended by Jimmy Witt and the hosts had been beaten for the first time in four matches. Danny Heath’s side will be looking to get back to winning ways on Saturday when they travel to Leyton Orient.

Southend United U18s: Callum Taylor, Reiss Chandler, Ahmet Biler, Sam Brogan, Tommy Davis, Ergis Shala, Damaray Anyadike (Kenny Coker, 81), Cameron Brown (Freddy Eastwood, 59), Adetayo Adeooja, Oli Coker, Bobby Unwin. Substitutes not used: Jamie Grossart, Callum Burkey, Jimmy Wallace.