The 2005–06 season was Colchester United's 64th season in their history and their eighth successive season in the third tier of English football, League One. Alongside competing in League One, the club also participated in the FA Cup, the League Cup and the Football League Trophy. The season was hugely successful for the U's as they achieved their first-ever promotion to the second tier of English football by finishing second in League One. They finished runners-up to Essex derby rivals Southend United by three points. Southend were successful in beating Colchester home and away across the season. Colchester had another long set of cup runs, reaching the fifth round of the FA Cup where they were defeated 3–1 by Premier League champions Chelsea at Stamford Bridge. They had beaten Leamington, Shrewsbury Town, Sheffield United and Derby County en route to the tie with Chelsea. They also embarked on a Football League Trophy run, once more reaching the area final but lost 3–1 on aggregate to eventual winners Swansea City. Season overview Colchester started the new season poorly. At the end of August after six games, they found themselves in the relegation zone with one win and two draws. Phil Parkinson had made a number of changes to his playing staff over the summer with numerous outgoings. He had signed Chris Iwelumo from Alemannia Aachen on a permanent basis and brought in Mark Yeates on loan from Tottenham Hotspur. It wasn't until Jamie Cureton arrived on loan from Swindon Town that the U's had an upturn in form as they earned five consecutive wins and went eight matches unbeaten. By Christmas, Colchester were in the top four but their unbeaten run was ended by Swindon on Boxing Day. They recovered from this setback to embark on another winning streak, earning seven wins on the bounce, ten matches including cup ties and sat top of the table by the end of January. Their form fell away in mid February and through March into April when they picked up just one win in 10 games, dropping from the automatic promotion places to the play-off spots. Meanwhile, in the FA Cup, Colchester had progressed to the fifth round to set up a tie with Premier League champions Chelsea at Stamford Bridge. The club equalled a 44-year-old record by beating Leamington 9–1 in the first round, and then saw off the challenge of Shrewsbury Town,