Despite twice holding a first-half lead, Southend United U18s were defeated 4-2 by Gillingham in their first away fixture in the EFL Youth Alliance Merit League One.
Jon Benton scored after six minutes with a trademark free-kick and Terrell Egbri netted in sensational fashion after 20 minutes, but on each occasion Blues were pegged back and the hosts went on to score twice in sixty second-half seconds to secure their win.
Blues were hit by a double-blow in their goalkeeping ranks as Harry Seaden missed out through illness and Callum Taylor - who has just been called up once again to the Northern Ireland U16s squad - was unable to make his debut through injury. U15s shotstopper Callum Hazeltine was handed his own inaugural appearance between the sticks.
Gillingham forced some early pressure with a couple of set-pieces once the match got underway following a half-hour delay to allow the overnight frost at Beechings Cross to thaw, but it was Dave Huzzey's side who took the lead when Benton was fouled 25 yards from goal. The midfielder brushed himself down to dispatch the dead ball delightfully into the top left-hand corner of the net.
The advantage lasted just a minute. Gillingham earned a free-kick of their own on the left touchline and the ball was delivered to the far post, where it was nodded back into the danger area for an attacker to score with an overhead bicycle kick that dropped inside the left-hand upright.
Blues bounced back and, after Matt Rush had seen his half-volley on the turn brilliantly palmed away by the Gills goalkeeper, Egbri smashed home his first U18s goal in unstoppable fashion. Seizing on a misplaced pass in midfield, the winger lined up a sweet left-footed strike from over 25 yards out that flew into the top left-hand corner.
Blues could have extended their lead five minutes later when Benton found Rush and his dipping effort whistled past the angle of post and crossbar, but they were indebted to Hazeltine just before the half-hour mark when he pushed a strong shot wide. However, Gillingham levelled again on 35 minutes when another free-kick was nodded down at the far post and an attacker volleyed home.
Despite the setback, Southend could have restored their advantage before the break, firstly when Rush stabbed into the side-netting after pouncing on a slip and then, in the final minute, when Benton's corner dropped to Marah at the back post and he poked wide.
Again there were opportunities at the beginning of the second period. Marah combined with Eren Kinali but could only locate the side-netting within two minutes of the restart, and the powerful forward was thwarted by the goalkeeper on 57 minutes after being released by a Benton through-ball.
In-between an attacker got the better of Miles Mitchell-Nelson and chipped off-target, and Gillingham moved ahead for the first time in familiar circumstances on 69 minutes when a left-wing centre was touched into the path of an attacker 12 yards out and he slotted past Hazeltine.
Within seconds 3-2 became 4-2 as Blues failed to put pressure on a home player 30 yards out and his strike was allowed to ping in off the left-hand upright, leaving Blues with a mountain to climb.
A Gillingham forward nodded over from close-range with a quarter-of-an-hour remaining, but it was Southend who ended strongly and were unfortunate not to score a third goal, which may have caused some anxiety for the Gills, in stoppage time.
Marah was denied by the woodwork when he met a Benton corner ten yards out and he fired against the crossbar, and substitute O'Shane Stewart also went close when his 20-yard effort was deflected wide, but Blues will now be seeking a first Merit League triumph at home to Bristol Rovers on Saturday (kick-off: 1:00pm).
Southend United U18s: Callum Hazeltine, Dan Humphreys, Rob Howard, Zak Pianim, Sam Knock, Miles Mitchell-Nelson (O’Shane Stewart, 72), Eren Kinali, Jon Benton, Sewa Marah, Matt Rush, Terrell Egbri.
Goals: Benton (6), Egbri (20).