July begins with Blues duo Tes Bramble and Shane Wardley appearing before magistrates in Ipswich jointly charged with assaulting a man in an Ipswich nightclub with the pair both pleading not guilty. The case is adjourned to August. Goalkeeper Daniel Gay signs from Norwich City while Leon Cort, a central defender from Millwall and striker Jason Harris from Hull both sign one year contracts. Blues pre-season friendlies include wins over Hendon (4-0), Grays (1-0), Bury Town (2-1). Followed up with a draw at Kingstonian (2-2) and a 2-1 defeat at Roots Hall to Peter Taylor's Leicester City (Pictured). A 1-1 draw with Canvey Island is followed with a 2-0 victory at Billericay Town. Meanwhile Blues sign Barnet striker Tony Richards for £36,000. 
August begins with a 1-1 friendly draw with Gillingham at Roots Hall. Blues sign Dean Holness, who had been appearing in Sky TV's Dreamteam programme, on a three-month contract. Martyn Booty signs for second division Chesterfield while Carl Hutchings re-signs for Blues 24 hours before the opening league fixture with Darlington. Blues begin their 2001/2002 campaign with a 1-0 win over Darlington despite losing Damon Searle midway through the first-half after he was shown a red card for a foul on former Blues striker Barry Conlon. Shane Wardley is cleared of the alleged assault charge while Tes Bramble's case is adjourned to September. Stuart King, signs a month's contract after being released by Preston North End. Blues first away game of the season sees them draw 0-0 at Mansfield. Blues go out of the Worthington Cup at the first hurdle when they lose to last seasons finalists Birmingham City 3-0 at St Andrews. The Shrimpers miserable night is compounded with the sending off's of Mark Rawle and Leon Cort (Pictured tackling former Shrimper Tommy Mooney). The day before Blues are due to play Halifax at home David Webb goes to hospital for a check up and is advised to stay away from Roots Hall to avoid stress. With Rob Newman in charge Blues storm to a 4-1 win over Halifax. Bank holiday Monday sees Blues go down 2-0 at Luton where Mark Rawle was sent off for the second time this season.
September begins with a 2-1 home defeat to local rivals Leyton Orient. David Webb returns back to work after his lay off and brings in a fitness guru to put the players through their paces. Blues make their first ever trip to Nene Park, the home of Rushden & Diamonds, and come away with a 1-0 win. Barrington Belgrave signs from Yeovil Town for £40,000 on a two-year contract. However, Belgrave's debut at Roots Hall v Hartlepool is a disappointing 0-0 draw. A midweek trip to Bristol Rovers results in last minute 2-1 defeat while the following Saturday sees possibly the worst performance of the campaign so far losing 2-0 at Oxford United's Kassam's Stadium. Blues get back to winning way with a midweek 3-2 victory over Carlisle at Roots Hall but then lose 2-1 to Cheltenham, also at Roots Hall.