October begins with David Webb announcing that he is to take time out to consider his future
and in the meantime Rob Newman will take charge of team affairs. A long Friday night haul to Torquay results in a 2-1 defeat as Blues slump down to 15th place. The following week David Webb holds a press conference to announce his resignation as Southend United Manager with Rob Newman taking over as Caretaker Manager. Mark Beard re-signs for Southend United after a year away playing at Kingstonian after previous Blues Manager Alan Little had released him. Newman's first match in charge as Caretaker Manager is a 4-2 win over Swansea City which is followed up with a 4-1 win at Conference side Stevenage Borough in the first round of the LDV Vans Trophy. Newman's superb start to life as Blues Caretaker boss is brought to a sudden halt at York where the home side come out on top 2-1. However, the defeat doesn't prevent Newman's chances of becoming Southend United's next Manager as the club officially announces the decision the following Monday. Newman's first official game in charge is a 2-1 defeat at Scunthorpe, which is a fifth consecutive away league reverse. A Carl Hutchings goal after just two minutes is enough to beat Kidderminster (Pictured) at Roots Hall although Blues go out of the LDV Vans Trophy with a 2-1 defeat to Bristol City at Roots Hall.
November begins with a sixth consecutive away defeat at Exeter 2-1. Rob Newman begins a clearout at Roots Hall releasing three players and placing five on the transfer list. A return to winning ways is achieved with a 3-0 victory over a poor Macclesfield Town side at Roots Hall. FA Cup first round action came to Roots Hall in November when Blues went through to round two with a thrilling 3-2 victory over Luton Town. League leaders Plymouth Argyle were next up at Roots Hall where the visitors recorded their first victory in Southend for 46 years with a 1-0 win. Former Blues striker David Crown is appointed as Newman's number two but is unable to prevent Blues going down 2-0 at Shrewsbury. Goalkeeper Mel Capleton, who missed most of the previous season with a broken leg, leaves Roots Hall along with Jason Harris, both leave by mutual consent.
December opens with a 1-1 draw with Lincoln City at Roots Hall. The following Saturday Blues are back in FA Cup action when they force a replay drawing 1-1 with Chesterfield at Saltergate. Daniel Webb leaves Roots Hall to join up with Brighton & Hove Albion on loan until the end of the season with a view to a permanent move. Southend United halt their slide of seven consecutive away defeats with a 1-0 win at Rochdale. The match sees Blues boss return to league action in a five-man defence at the age of 37. The superb victory at Rochdale was followed with 2-0 FA Cup replay win over Chesterfield at Roots Hall. A 0-0 draw at promotion chasing Hull City was followed by a storming second-half comeback against Rushden & Diamonds at Roots Hall on Boxing Day. 
Looking ahead to 2002 Blues can look forward to a Third Round FA Cup tie at home to Second Division Tranmere Rovers. Meanwhile Blues are 12th in the Third Division table and seven points off a play-off place. Sounds familiar doesn't it, yes its where we started twelve months ago. However, nothing is certain in football and one thing for sure it will never be dull with Southend United.