Southampton's B team suffered a cruel late defeat in their EFL Trophy opener at Stevenage, with the winning goal coming two minutes from time.
Callum Slattery opened the scoring for Saints in the 37th minute with a free kick which took a cruel deflection as far as Stevenage were concerned to take it past Jamie Cumming.
But despite impressing during the opening 45 the visitors did not go into the break ahead, Marcus Dinanga equalising for Alex Revell’s side in the third minute of three added on.
The winner came two minutes from the end; Tyrone Marsh connecting from close range in the 91st minute.
Saints made four changes to the side that lost to Chelsea in Premier League 2 on Friday – Christoph Klarer, Tom O’Connor, Caleb Watts and Josh Sims making way as Yan Valery, Kayne Ramsay, Jake Hesketh and Kegs Chauke came in.
The hosts made seven changes following their League Two win at the weekend, also naming a 15-year-old, Sam Tinubu, alongside players on their substitutes bench with plenty of EFL experience, such as Elliott List and Scott Cuthbert.
One of the returning Saints players, Yan Valery, used his pace to his advantage early on down the left flank; firing in a dangerous cross which Stevenage did well to head clear after six minutes.
Despite the hosts winning a couple of early corners, Saints more than held their own in the opening stages against their more experienced opponents.
Dan N’Lundulu, under considerable pressure from Ross Marshall, was in one-on-one but could only drag his effort wide of the near post just shy of 12 minutes.
Another fine run from Valery was found by skipper Callum Slattery after 17 minutes, but the full-back’s low cross was cleared in front of the Stevenage goal before any onrushing Saints player could connect.
Saints continued to put their hosts under pressure during the opening half-an-hour, proving to be more than a match physical for the League Two side.
But it was indeed Stevenage went the closest on the evening, Femi Akinwande cutting inside and striking the post on 30 minutes as Saints cleared the rebound.
Saints continued to come forward, Hesketh winning a free-kick just outside the penalty area on 36 minutes for which the Stevenage skipper Romain Vincelot was cautioned for.
Slattery stepped up, firing his effort over the wall and towards goal, leaving keeper Cumming with little chance following a deflection off of Jack Smith.
Saints had chances to extend their lead as the half drew to a close, but the hosts had the last word of the half in the final minute of three added on.
Dinanga curled an effort across the face of Harry Lewis with the last kick of the first 45 to draw the scores level at the interval.
Buoyed by their strong finish to the first half, Stevenage came out for the second half firing; Tyrone Marsh played through within the opening minutes and skipping past Lewis, but his eventual cross not finding Inih Effiong cleanly.
Ramsay was next to show his defensive exploits; sliding in to deny Effiong inside the Saints penalty area just shy of the hour mark as the hosts piled on the pressure.
Jankewitz also didn’t shy away from any challenges, using his strength to hold off Smith and win a free-kick for Saints to relieve some of the pressure.
Will Ferry did brilliantly just after the 65th minute to bring down a Lewis goal-kick with his chest and brush past his nearest defender, before playing in Ramello Mitchell who just mistimed his run.
Valery was once again lively during the second half, beating two men with a barnstorming run inside the penalty area before finding N’Lundulu who can only shoot over from close range.
Stevenage then went close themselves; Akinwande drifting in from the left but only able to fire over from inside the box.
With penalties looming both sides battled with the ball, Ferry clattering with Akinwande in the air following a heavy challenge whilst Effiong was forced off for Stevenage after a strong Kazeem Olaigbe challenge.
Saints went even closer on the 90-minute mark; Hesketh cutting inside from the left flank and forcing a strong save from Cumming.
But in the harshest of circumstances the League Two side burst forward and found a winner in the 91st minute.
Akinwande finding Osborne who squared it to Marsh to put them ahead for the first time on the evening.
The game finished with the cruellest of score lines after what was a spirited performance from Southampton’s youngsters away from home.
Jamie Cumming (GK)
Romain Vincelot (C)
Inih EffiongArthur Read (85′)
Jack SmithElliot Osborne (62′)
Harry Lewis (GK)
Yan ValeryPascal Kpohomouh (0′)
Allan TchaptchetTom O'Connor (58′)
Callum Slattery (C)
Ramello MitchellKazeem Olaigbe (68′)