IPSWICH 3 BORO 1
Crossley, Stockdale (Dove 78), Davies, Cooper, Vidmar, Wilkshire, Wilson, Marinelli (Cade 66), Queudrue, Nemeth (Close 66), Johnston.
Subs Not Used: Gulliver, Russell.
Middlesbrough added to the Barclaycard Premiership casualties in round three of the Worthington Cup after being comprehensively outclassed by First Division strugglers Ipswich tonight.
Joe Royle's team never looked back after taking a second-minute lead at Portman Road, and the contest was all but over by half-time.
Boro fielded only Franck Queudrue and Szilard Nemeth of the side which lost the Tyne-Tees derby 2-0 to Newcastle 48 hours earlier as manager Steve McClaren chose a second-string team which included debutant 17-year-old centre-back Andrew Davies.
Even Ipswich rested a number of first-team players - with captain Matt Holland, Jim Magilton, Darren Ambrose and Wayne Brown all left out.
New Ipswich boss Royle responded to a striker crisis - Alun Armstrong, Marcus Bent and Richard Naylor were injured and Pablo Counago suspended - by pairing teenager Darren Bent with former European Cup-winner Finidi George.
But the Blues, as in the UEFA Cup this season, once again excelled against higher-grade opposition after gaining a perfect start through an unlikely source with their first foray forward.
Danish defender Thomas Gaardsoe started a move from just outside his own penalty area and continued his progress deep into the Boro half to run on to Jamie Clapham's probing pass, bursting past Robbie Stockdale on the edge of the box and beating Mark Crossley with a left-foot shot from a diminishing angle.
That incident aside, the opening stages failed to deliver much goalmouth action as both sides felt their way into the match.
Ipswich, employing wing-backs as opposed to their more accustomed 4-4-2 formation, created the next opportunity when hesitancy in the visitors' defence allowed George to tee up Fabian Wilnis whose goalbound shot struck Tony Vidmar in the midriff.
Wilnis was soon provider as his long ball allowed Bent to get ahead of the Boro backline and bear down on goal - but Vidmar recovered with a splendidly-timed tackle as the 18-year-old shaped to shoot.
Middlesbrough's first attack of note arrived in the 25th minute when Carlos Marinelli picked out Allan Johnston, who fired just wide from 20 yards.
Within seconds McClaren's side created a better chance as Johnston touched the ball into the path of Queudrue. But the Frenchman blazed over James Pullen - a 20-year-old goalkeeper making his debut - exposed in the home goal.
Luke Wilkshire forced Pullen into his first save - a swerving, long-range effort helped over the bar.
Ipswich had a second goal when George fed Tommy Miller, whose pass allowed Clapham to collect without breaking stride and beat Crossley from 18 yards with a fine finish.
The tie was all but over a minute before half-time when captain Colin Cooper's misplaced pass was seized upon by Wilnis whose cross was powerfully dispatched over Crossley and into the net by Bent's forehead.
Neither manager made alterations on the resumption, and Ipswich continued to pose the greater threat.
Bent, who scored the only goal in Ipswich's Premiership win over Boro on the same ground in April, continued to be their tormentor in chief.
Only a desperate clearance snuffed out a chance for the teenager three minutes in as Wilnis' cross-shot caused mayhem.
Then from a succession of Blues' corners, defender Chris Makin - who has not scored for the Suffolk club -- burst into the area and saw a shot deflected for a corner.
Middlesbrough should have registered a consolation 10 minutes from the end of a subdued second period, but the unmarked Wilkshire somehow prodded wide from 10 yards.
Yet they might have been four goals adrift when Bent produced a moment of brilliance, receiving Hermann Hreidarsson's pass after a powerful surge by the Icelandic defender and curling a 25-yard effort against the underside of the crossbar and then clear.
But Boro did decrease the deficit three minutes from time when Johnston slipped Queudrue into the area, and Pullen was beaten by a well-placed cross-shot from the left.