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Town were given a dream start on two minutes when Danish defender Thomas Gaardsoe races in to the box on to Jamie Clapham's pass and chipped Mark Crossley.
Ipswich dominated the early stages and could have scored again but for a well timed challenge by Tony Vidmar on Darren Bent as he chased a Fabian Wilnis throughball.
Middlesbrough came to life midway through the half as Alan Johnston shot wide from an angle and then Franck Queudrue shot over from Carlos Marinelli's pass.
Town weathered the storm and scored again on 40 minutes when Jamie Clapham collected Tommy Miller's pass and thrashed a rising drive beyond Crossley.
The visitors then gifted Town a third goal on 44 minutes. Colin Cooper's wayward ball was collected by Wilnis who crossed for Bent to head home.
Boro needed an early breakthrough to get back in the game, but instead it was Ipswich who continued to force the pace.
Robbie Stocdale made a last ditch tackle to foil Bent, then Chris Makin had a shot deflected over.
Bent came close to a superb second goal with seven minutes to go, only for his curling 25-yard shot to be kept out by the crossbar.
Queudrue fired a late consolation for the visitors but manager Steve McClaren may be ruing his decision to make nine changes from the side which had started Monday's 2-0 defeat at Newcastle.
| Kickoff 6 November 2002 19:45 at Portman Road | |
| Referee: Wolstenholme, E. K. | Attendance: 14,417 |
Final Result | |
Ipswich 3 | Middlesbrough 1 |
T.Gaardsoe (2) J.Clapham (40) D.Bent (44) | F.Queudrue (87) |
Yellow Cards | |
T.Vidmar, 57, unsporting behaviour B.Close, 77, unsporting behaviour M.Wilson, 89, unsporting behaviour | |
Red Cards | |
Match Squads | |
Ipswich 3 | Middlesbrough 1 |
1. J.Pullen 2. C.Makin 3. H.Hreidarsson 4. T.Gaardsoe 5. M.Venus 6. F.Wilnis 7. J.Wright 8. T.Miller 9. J.Clapham 10. F.George 11. D.Bent | 1. M.Crossley 2. R.Stockdale 3. T.Vidmar 4. C.Cooper 5. F.Queudrue 6. M.Wilson 7. A.Davies 8. L.Wilkshire 9. A.Johnston 10. C.Marinelli 11. S.Nemeth |
Substitutes | |
12. A.Marshall 13. M.Bloomfield 14. I.Westlake 15. M.Richards 16. R.Logan | 12. B.Close 13. P.Gulliver 14. J.Cade 15. C.Dove 16. S.Russell |