Yeovil added a new chapter to their giant-killing chronicles as they left Portman Road having beaten a woeful Town 2-0. The Glovers went ahead on the stroke of half-time through former Norwich trainee Darren Way, sub Kevin Gall adding a second three minutes from the final whistle.
Boss Joe Royle made a number of changes from the side which beat Sheffield Wednesday 2-1 on Saturday. Lewis Price returned in goal after his knee injury, while Aidan Collins and Jimmy Juan came in for their first Town starts and Jaime Peters his first start at Portman Road. Fabian Wilnis, Shane Supple and Owen Garvan all dropped to the bench with Jim Magilton not in the squad.
The Blues lined-up in a 4-3-3 formation with Peters wide on the left, McDonald on the right and Bowditch in the centre. Town's first chance of the game was created by McDonald, the former Arsenal trainee crossing to the far post where Peters headed wide.
McDonald caught Colin Miles in possession a minute later but put his shot across the face of goal. Naylor was similarly caught dawdling by Matt Harrold, Lewis Price grabbing the Yeovil striker's 25-yard shot after palming it into the air.
Way headed a Harrold cross straight at Price before Skiverton picked up a yellow card for a late tackle on McDonald.
Currie and then Bowditch put shots wide from the edge of the penalty area prior to Currie trying to catch Chris Weale off his line with an ambitious chip from distance but the Yeovil keeper was quickly back to claim on his line.
Arron Davies shot wide from a Kevin Amankwaah cross in the 31st minute and soon after a Lee Johnson freekick flashed across the area and somehow avoided a crowd of players.
Town's brightest moment of a low-key and generally dull and uninspiring half came when Matt Richards broke forward and exchanged passes with Dean McDonald before hitting a low shot straight at Weale.
Sito created a chance for Dean Bowditch in the 40th minute, the England U19 international taking a touch but miscuing his volley wide.
Bowditch forced Weale into his only serious save of the game a minute later, the keeper pushing the 19-year-old's well-struck edge-of-the-area effort wide.
As the players were starting to look forward to their half-time cuppa, Lee Johnson whipped in a corner from the Yeovil right and an unmarked Darren Way headed powerfully into the net, catching Matt Richards unawares on the post.
Yeovil's goal provided an undesirable end to an anticlimactic half, the game having been played in an atmosphere more akin to a pre-season friendly than a cup-tie. The expected slick and invigorated Town, so impressive on Saturday, never appeared and many of the 11,299 who had bothered to attend must have wished they'd stayed at home and saved themselves £15.
Joe Royle was evidently equally unimpressed and made three changes. Off came Jimmy Juan, Jaime Peters and Darren Currie with Ian Westlake, Fabian Wilnis and Owen Garvan replacing them. Wilnis went to centre-half with Richard Naylor moving up front alongside Dean Bowditch, while the other two subs took up their regular positions in midfield.
Bowditch failed to take down a Westlake ball from the left in a promising position in the 49th minute but Town's best chance of the game came three minutes later. McDonald played in Naylor on the left of the area, the stand-in skipper taking the ball past the keeper but taking it wide. Town's 2000 play-off final hero got in a shot but Skiverton put the ball over the bar.
From the resultant corner, Wilnis headed McDonald's deep cross wide. Town were looking much more of a threat in the early stages of the second half.
Neither side created too much but just ahead of the hour mark Way shot over from 25 yards at one end and Westlake went closer with a 20-yard strike at the other. Shortly afterwards, Aidan Collins did well to cut out a dangerous freekick sent into the Town box by Lee Johnson.
Efetobore Sodje headed a corner wide, prior to Richards teeing-up Westlake who shot over from 20 yards.
Way sent the ball across the face of the Town goal, then Kevin Horlock wasted a freekick from just outside the area, the midfielder's curled effort flying harmlessly over the bar.
Sito received his first yellow card in English football in the 77th minute for a tackle on Nathan Jones, the Spaniard convinced he had won the ball.
With the Blues pushing for an equaliser, Yeovil broke away and scored a second goal. Collins did well to get back and tackle sub Kevin Gall but the striker managed to get back on to the ball and was given time to pick his spot and slip the ball past Price.
In injury time, with many of the crowd already making their way home, Westlake struck a shot from the left of the penalty area which flew inches wide.
Town's dire Carling Cup record continues, the Blues having been beaten by Doncaster last season and Notts County a year earlier. Town appear to have little serious ambition when it comes to cup competitions these days and the attendance at next season's Carling Cup fixture is unlikely to surpass the 10,000 mark unless ticket prices are further reduced.
The only plus for the Blues was the excellent display from Aidan Collins, making his first senior appearance since his debut as a sub at Derby on the final day of the 2002/03 season. The 18-yeqar-old looked composed, strong and certainly capable of providing back-up to Town's senior central defenders.
Jimmy Juan failed to impose himself on the game in the first half despite one or two clever passes, while Peters was again less impressive as a starter than he has been as a substitute. McDonald wasn't as effective as he was on Saturday but overall the Blues lacked a creative spark throughout - Jim Magilton's influence very much missed - despite enjoying a lot of possession in the second half.
Town: Price, Sito, Richards, Naylor, Collins, Horlock, Juan (Westlake 46), Currie (Wilnis 46), Peters (Garvan 46), Bowditch, McDonald. Unused: Supple, Barron. Att: 11,299.