Two points for Town following penalties victory
Town progressed to the knockout stages of the Papa John's Trophy courtesy of a penalty shootout victory over Colchester.
After a goalless draw, the visitors' Chay Cooper hit the post with the final spotkick as the Blues sealed second place in Southern Group A.
Ed Schwartz, the representative for ORG who own 90% of Gamechanger 20 Ltd, was in attendance for his first Town fixture following on from Three Lions fund member, Brett Johnson, visiting Ipswich last month.
Paul Cook made nine changes to the side who drew 1-1 against Oldham in the FA Cup on Saturday, Kane Vincent-Young and Cameron Burgess being the only players to retain their place in the side.
Ex-Town skipper Luke Chambers and forward Freddie Sears were two of four former Blues in Colchester's starting XI, ex-goalkeeper Dean Gerken also named amongst the substitutes.
It was one of that contingent, Sears, who created the first chance of the game. After winning the ball deep inside Town's half, the now U's striker played a dangerous low ball across the face of goal which Vincent-Young was forced to turn behind for a corner.
Cook's side cleared and forged their own opening at the other end a minute later, Joe Pigott stinging the palms of Jake Turner from the edge of the box after being teed up by Louie Barry.
Sears looked dangerous again shortly afterwards, Vaclav Hladky racing out of his goal to deny him on his Portman Road return.
Pigott, who had seen a header disallowed for being offside earlier in the half, went even closer at the other end, his powerful strike from a tight angle being palmed onto the post by Turner before Barry couldn't direct his volleyed rebound on target.
In what was an end-to-end opening half an hour, Luke Hannant had a well-struck effort blocked by Luke Woolfenden from the middle of the box.
Sears and Conor Chaplin both saw low driven shots parried away early in the second half, Barry's shot being blocked following a corner after the latter.
Chaplin looked to turn provider with just over an hour played, Scott Fraser collecting his clipped pass over the top of the backline before his shot was well-saved by Turner.
Bersant Celina, Town's third sub midway through the second period following the half-time introductions of Wes Burns and Bailey Clements, saw a deflected effort from just outside of the area collected by U's 'keeper seconds after coming on, Pigott having a curling shot tipped over the top of the bar a few moments later.
Cooper had a golden opportunity to win it in stoppage time but, following a mix-up at the back for Blues, the Colchester sub shot wide of an empty net from 25 yards.
Pigott and Sears missed the opening penalties of the shootout with both sides netting the next three apiece. Sone Aluko fired Town's fifth into the top corner before Cooper was denied by the woodwork from his own spotkick as the Blues progressed to the knockout stages.
Town: Hladky, Vincent-Young (Burns 45'), Woolfenden, Burgess, Kenlock (Clements 45'), Harper, Fraser, Aluko (C), Barry (Celina 71'), Chaplin, Pigott.
Subs: Holy, Donacien, Evans, Jackson.
Colchester: Turner, Chambers (C), Wiredu, Hannant, Nouble, Sears, Chilvers, Eastman, Kennedy (Cooper 60'), Tchamadeu (Welch-Hayes 67'), Daniels (Coxe 84').
Subs: Gerken, Welch-Hayes, McCoulsky, Thomas, Tovide.
Attendance: 8,100 (566 Colchester fans).