Matthew Takawira scored a 97th-minute winner as the Under-21s broke their Premier League Cup duck with a fine 2-1 win at Reading on Monday night.
The Town lost all six matches in the competition last season and their opener to Burnley earlier this month this term.
But Alex Lawless’ side dug deep in Berkshire to earn a historic victory thanks to Takawira’s late, late show.
The Town had the first chance five minutes in when Josh Phillips rolled a shot wide but an even first half ended goalless.
However, the Hatters took the lead just two minutes into the second period. Half-time substitute Tyrell Giwa found himself one-on-one with the Reading defence before cutting inside a firing a low effort into the bottom corner.
The Town’s advantage would last 14 minutes as shortly after the hour mark the Royals levelled in stylish fashion when Tivonge Rushesha powered a brilliant half-volley from outside the box past Liam Coyne.
Coyne then needed to be alert as the home side went in search of the lead, the Hatters goalkeeper producing an excellent save to deny Joe Barough with six minutes left.
It would prove to be crucial as, just when it seemed the game would peter out to a draw, substitute Takawira bunded home Jacob Pinnington’s right-wing cross deep into injury time to spark wild scenes of celebration from the Town contingent.
Town: Coyne, Pinnington, Chigozie, Kayibanda, Bateson, Paternoster, Lorentzen-Jones (sub Takawira 76), Martins, Harris (sub Trustram 38), Phillips, Benagr (sub Giwa 46).
Subs not used: Booth, Stitt.