The 2005–06 season was Colchester United's eighth consecutive season in the third tier of English football. The season ended in success with Colchester's first ever promotion into the second tier of English football when they finished 2nd in League One. In addition, they had good cup runs in the FA Cup, being knocked out by then Premier League champions Chelsea in the 5th round, and finished as area finalists in the LDV Vans Trophy.

The season kick started with the arrival of Phil Parkinson's old Reading team-mate Jamie Cureton on loan from Swindon.

U's were in the top four by Christmas and their 12-match unbeaten run was halted at Swindon on Boxing Day. Parkinson's side simply embarked on another run of seven straight wins, 10 if Cup ties are included, and topped the table in January 2006. Once again United reached the LDV Southern Area Final but losing to Swansea City. The FA Cup brought more success on and off the pitch. Poor Leamington were thrashed 9-1 in the First Round on 5 December 2005, equalling a 44-year club record. U's won at Shrewsbury and then beat Championship sides Sheffield United and Derby to set up a mouth watering tie at Chelsea.

José Mourinho's side had been assembled for around £225m whilst United were valued at £150,000. More than 6,000 fans in the 41,810 live televised game witnessed the incredible, as Carvalho's own goal put United in front. Chelsea threw on their big guns Joe Cole, Frank Lampard and Hernán Crespo to win 3-1. United captured a little piece of worldwide acclaim and a huge bonus to their bank balance, but league form dropped alarmingly. U's won just one in 13, including Cup ties, went seven out of eight League games in February without scoring and lost the top of the table clash with Southend by 3-0 at Layer Road.

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