Southampton earned their first point of the Checkatrade Trophy campaign with a penalty shoot-out defeat to Charlton at the Valley.
After a goalless 90 minutes in south east London, the first group stage game went to spot-kicks to decide which team would get an extra bonus point for winning a contest from 12 yards.
Saints, who had earlier missed a penalty in the first half of the game, were beaten in the round of spot-kicks as the Addicks triumphed 5-4 on penalties.
This was the first of three games in the group stage of the revised Football League Trophy competition, in which Saints, as a Category One Academy club, must field six players in the starting eleven who are under the age of 21, while their opponents must field at least five first team players.
Harrison Reed captained the visiting team, in a match which also saw goalkeeper Alex McCarthy make his first appearance in a Southampton shirt.
Jack Stephens, Harrison Reed, Jake Hesketh and Sam McQueen were all absent over the weekend, but Technical Director Martin Hunter brought them into this side, with the latter continuing his development at left back.
The hosts got the game under way and they had the first chance of the game too, as early as the third minute, when defender Morgan Fox drove a low strike across the face of goal, which McCarthy got a hand to.
Saints grew into the game though and were a threat on the break. Harrison Reed whipped a free-kick wide of the right post after Olufela Olomola had been brought down.
Reed had an even better chance in the 22nd minute however, when Saints were awarded a penalty. It came after Jake Hesketh was alert to a rebound from a free-kick before he was brought down by Andrew Crofts to give Martin Hunter’s side a chance to take the lead.
Reed stepped up from 12 yards but screwed his effort wide of the left post with ‘keeper Dillon Phillips also a whisker away from getting a touch on it.
Either side of the half hour mark Sam McQueen had two opportunities from free-kicks just outside of the area, the latter of which drew a smart save from Phillips diving low to his right.
Olomola also forced a decent save from Phillips to his left with a shot that was destined for the bottom corner.
At the other end, Karlan Ahearne-Grant headed an effort over, before Saints defender Alfie Jones made a terrific block to deny Brandon Hanlon a shot at goal before the half-time whistle, leaving the game scoreless after 45 minutes.
Charlton made a stronger start to the second half, but McCarthy remained largely untroubled as Chris Solly drove a shot wide, while Ahearne-Grant could only find the side-netting from close range.
Saints were neat in possession and created a couple of good openings past the hour mark when first Olomola laid the ball back to Gape, who curled a lob wide, before Olomola then had a chance of his own as he headed an effort at Phillips inside the six yard box.
Substitute Joshua Umerah had the Addicks’ best chance on 75 minutes when he robbed Valery of the ball on the right before facing up one-on-one to McCarthy, but the Saints stopper produced a low save to keep the effort out.
McQueen struck another long range shot which forced Phillips into another save at full stretch, before Sims hit a rising strike at the Charlton ‘keeper as the visitors took the game to spot kicks by keeping the score at 0-0.
Both teams missed a penalty in the first five spot kicks taken, with Charlton’s Ezri Konsa scoring the Addick’s sixth penalty, while Saints ‘keeper Alex McCarthy stepped up to take the visitors’ last effort which crashed back off the crossbar.
Next up for Saints in this competition is a trip to Colchester United in October.