Town crashed out of the U21 Premier Cup at the round of 32 stage as a 65th minute Sam McQueen goal gave Southampton a 1-0 victory at Portman Road. The Blues, who fielded trialist Sean St Ledger, were the better side in the first half but the Saints were on top after the break.
Former Ireland international defender St Ledger started for the Blues at the centre of the defence. A free agent following his release by Leicester in the summer, the 29-year-old was previously close to joining Town in January 2012 before regaining his place in the Foxes side.
The Blues created the first chance of the game in the fourth minute, Balint Bajner cutting the ball back from the right to left-back Ben Wyatt who blazed over from the edge of the box when he should have hit the target.
Town continued to have the better of the early stages, although all too often running into trouble prior to creating any significant danger. On 11 Cameron Stewart hit a weak 25-yard effort which failed to test Saints keeper Paulo Gazzaniga.
Southampton went close for the first time on 14, Ryan Seagers hitting a shot which deflected off Blues skipper Matt Clarke and flew just wide of keeper Michael Crowe’s left post.
A minute later, Henshall saw a strike deflect wide, then trialist St Ledger took an accidental boot to the head from Saints defender Niall Mason but was fine to continue.
Town should have gone ahead in the 18th minute when Gazzaniga got nowhere near Henshall’s right-sided corner, but the ball flicked off Clarke’s head and bounced wide of the post.
The Blues went close again a minute later, Stewart unleashing a powerful 25-yard strike which Gazzaniga blocked but couldn’t hold onto. The loose ball bounced over Darren McQueen to Bajner, who was unable to get over his volley and found the middle of the lower tier of the Sir Alf Ramsey Stand.
Hungarian striker Bajner had started promisingly though, and on 22 he wriggled through a number of challenges on the edge of the box before shooting over from an angle on the right.
The Blues continued to dominate and just before the half-hour mark central midfielder Victor Guldbrandsen, a recent signing from Danish club Lyngby, turned an Emmanuel cross from the right wide.
Trialist St Ledger had been largely untested but in the 35th minute he did well to intercept a ball played in for Isgrove, although failed to get too much distance on his left-footed clearance.
Despite the Blues having had most of the game, the visitors had looked a threat on the break and on 41 Wyatt misread a long ball down the right, allowing Omar Rowe a run at goal. Fortunately for the full-back Crowe was off his line quickly to block.
Crowe was in action again moments later after Town had failed to clear on the edge of their box. The ball eventually fell to Isgrove, who shot straight at the Blues keeper.
Four minutes after the restart, Blues midfielder Kundai Benyu forced Gazzaniga into the first save of the second half, the Saints keeper plucking his 25-yard effort out of the air to his left.
A minute later, St Ledger perhaps showed his lack of match fitness when he misjudged a tackle as Rowe took the ball past him midway inside the Town half.
As the game moved towards the hour, Seagers headed a Saints freekick straight at Crowe from close range.
Then, on 63 Southampton striker Sam McQueen was played through in on goal but chipped over the bar as well as Crowe when he should have hit the net. The Saints frontman was probably glad to see a linesman’s flag raised.
Two minutes later with the visitors increasingly on top, McQueen did find the target, cutting in from the right past Clarke before smashing an unstoppable shot across Crowe and into the corner of the net to give his side the lead.
The Blues lost Cameron Stewart, who had been lively before the break, to what looked like a hamstring injury in the 68th minute, Cory Galvin taking over.
Rowe lashed well over in the 72nd minute when he ought to have done better having been found by Isgrove in space on the left of the area after an impressive run from the former Peterborough loanee.
The fast-breaking Saints were looking more likely to add a second goal than Town were to equalise with too many Blues crosses hitting the first man.
Southampton sub Josh Sims almost scored with his first touch on 77 but flicked a cross from the left well wide.
The Premier League side had been on top having got their noses in front and in the 87th minute were close to adding to their lead when Seagers found Sims on the left of the area. The sub cleverly turned and hit a low shot which Crowe did well to save down to his left.
The Blues were unable to threaten again before the referee blew his whistle and their short U21 Premier Cup run was at an end.
Town had been the better side before the break but failed to make the most of their period in the ascendency, Wyatt, Clarke and Bajner having decent chances to open the scoring.
In the second half, the Saints were on top and in the end had enough chances to have won the tie more comfortably.
Trialist St Ledger unsurprisingly appeared a little short of match sharpness at times, making one or two errors which looked down to his recent lack of games, particularly in the closing stages of the match. However, overall he looked comfortable for the most part.
After the game, he tweeted: "So, after all the rumours over the years I put on a Ipswich Town shirt tonight! Felt good!"
Watching manager Mick McCarthy will have been disappointed to see Stewart suffer yet another injury, while Bajner had a more effective first half and skipper Clarke and midfielder Benyu again impressed.
U21s: Crowe, Emmanuel, Wyatt, Guldbrandsen, St Ledger, Clarke, Stewart (Galvin 68), Benyu, McQueen, Bajner, Henshall. Unused: Marsden, Robinson, McLoughlin, Galvin, Ford.
Southampton: Gazzaniga, Mason, DeBayo, Gape, Mugabi, McCarthy, Isgrove, Little, McQueen (Sims 76), Seagers, Rowe. Unused: Cook, Istead, Willard, Lea. Referee: Alan Young.