The 2008–09 season was Colchester United's first season back in the third tier of English football after being relegated from the Football League Championship.

Life at the new stadium began with the announcement of a sponsorship deal that would see it being named The Weston Homes Community Stadium. The first-ever match was a reduced capacity ramp-up event against Spanish side Athletic Bilbao on 4 August 2008. Scott Vernon had the honour of scoring U's first goal at their new home as 5,610 watched a 2-1 defeat.

Fans favourite Karl Duguid left in the summer to pursue Championship football with Plymouth and Kevin Lisbie joined neighbours Ipswich for a reported £650,000 fee. Short on firepower, manager Geraint Williams broke U's transfer record yet again, bringing in Cheltenham's Steven Gillespie for £400,000.

In order to iron out any teething problems, United were granted permission by The Football League to play their first two games away from home, and thus the first-ever League fixture came on 16 August against Huddersfield when a 0-0 draw was played out. Mark Yeates became the first U's scorer in a competitive match at WHCS when he bagged both goals in a 2-2 draw with Oldham on 30 August. United couldn't force a win at home and following a 3-0 home defeat to MK Dons that left United in the bottom four with a record of 1 League win from 6, Williams was relieved of his duties.

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