Town's U18s were well-beaten 3-0 by Bury Town at Ram Meadow on Tuesday evening as the non-league side reclaimed the Martin Swallow Memorial Trophy, with two of their three goals coming via former Blues academy players.
The West Suffolk side won the inaugural trophy in 2021 but Town then won it for the last three seasons, although fielding U21s sides.
Despite this evening's fixture being advertised as such, it was very much an U18s team that played, with the Town U21s losing 1-0 at home to Colchester United in a behind-closed-doors friendly at Playford Road earlier in the day.
The young Blues, playing in the new red away kit, had the first chance on 12 when a good long pass forward from keeper Will Fletcher found Shak Nicolaou (pictured) and the former Spurs attacker forced home stopper Charlie Beckwith into a good save at his near post.
Nicolaou then hit a low snapshot from just outside the box, which Beckwith parried away, but at the other end the side managed by former Town midfielder Cole Skuse took the lead on 26.
A George Quantrell cut-back from the left byline struck the hand of a trialist centre-back from close range but referee Chay Hathway pointed to the spot and ex-Town academy striker Cemal Ramadan stepped up to convert.
Bury doubled their lead just three minutes later when Mikey Davis's corner from the right evaded a crowd of players and was touched home at the back post by centre-back Taylor Parr.
The momentum of the game had clearly swung and it was only an offside flag that denied the hosts a third goal in just nine minutes. A long throw was headed goalwards by Parr and the ball glanced off an attacker inside the six-yard box before ending up in the net, but the Town youngsters were relieved to see the flag raised.
Shortly before half-time, some quick one-touch passing from the home side on the edge of the Town box resulted in another former Town academy youngster, Tommy Hughes, firing over from a good position.
Despite going into the break just two goals behind, David Wright and Matt Pooley's side made the worst possible start to the second half as they conceded a third goal within 15 seconds of the restart.
Fletcher's clearance hit the unfortunate Bobby Sains just inside the area and fell kindly to the third ex-Blues youngster in the home side, Harley Curtis, who stroked the ball into the unguarded net with ease.
Fletcher was then out quickly to make a smart block from Davis after a fine sliderule pass from Ramadan, before various substitutions from both sides somewhat disrupted the flow of the second half.
After Nicolaou's couple of chances early on, Town had really failed to test Beckwith and it wasn't until the 74th minute when one of the Town subs, Indianna Pedder, dispossessed Ethan Mayhew on the edge of the box, but his low shot across goal went wide of the far post.
Six minutes later a cross from the Town right side wasn't properly cleared and Pedder hit a crisp volley that was well tipped over by Beckwith.
The only other chance of note in the remaining ten minutes was a header from a corner from Town's trialist defender, which the Bury keeper gathered comfortably.
Overall it was a difficult night for Town's teenagers against a well-drilled Bury side who are looking forward to a new test at Southern League Premier Division Central level following a dramatic promotion last season.
U18s: Fletcher, Brouwers, P Adebayo (Brown 76), Trialist, O'Sullivan, Sains (Boakye-King 76), Trialist (Nsofor 62), Wood (Buskell 62), Burton-Yurevich, Ekontosia (Pedder 62), Nicolaou. Unused: Wreford. Att: 481.