April begins with a midweek trip to Darlington where Tes Bramble scores his first goal for the club in a 1-1 draw. This is followed up with 2-1 victory over Hartlepool at Roots Hall and a 2-2 draw at Exeter despite Blues storming into a 2-0 lead. April was also a sad month for everybody connected with Southend United when match referee Mike North tragically collapses and dies on the Roots Hall pitch two minutes before half-time in the league match v Mansfield Town after suffering a heart attack. The match was subsequently abandoned. Following the tragedy surrounding Mr North's death Southend United announce that all proceeds for the rearranged game will go to Mr North's family. A 28th minute penalty condemns Blues to a 1-0 defeat at Macclesfield that leaves Blues in 11th place and their play off hopes fast decreasing. Home Park, Plymouth was Blues next port of call. In a thrilling match Blues quickly went two goals down only to pull it back to 2-2 in the second-half. However with minutes remaining on the watch Plymouth re-take the lead only for Blues to sensationally equalise in the dying seconds. The following day the funeral of Mike North takes place, which is attended by Blues Manager David Webb. Blues then disappointingly draw 1-1 at home to Carlisle to virtually condemn Southend United to another season in Division Three 
May began with Hull City securing a play off place with a 1-1 draw at Roots Hall. Blues ultimate away game of the season sees them go down 2-1 to Cheltenham Town. The rearranged game with Mansfield Town is allowed to take place the Tuesday after the season has officially finished. The match is attended by Mr North's wife and Brother who both bravely stand on the edge of the centre circle as a minutes silence is impeccably observed. Blues win the match 3-1. Kevin Maher is announced as the Player-of-the-Season and Blues finish their campaign in 11th place with a record of having won - 15, drawn - 18 and lost - 13, amassing 63 points. After the Mansfield game David Webb immediately begins rebuilding for the following season releasing Michael Black, Ben Abbey and Russell Williamson while David Lee, Darryl Flahavan and Scott Forbes are offered one-year contracts. Martyn Booty is officially placed on the transfer list. David Webb makes his first summer signing - 19-year-old Gareth Risbridger from Yeovil Town. Darryl Flahavan accepts Webb's contract while David Lee leaves Roots Hall to join Hull City.
Player-of-the-Season 2000/2001
June sees Assistant Manager Mick Gooding (pictured) leave by mutual consent while Scott Forbes signs a one-year contract. David Webb makes his second summer signing when he returns to Yeovil to sign Chelmsford born Ben Smith. Stephen Broad completes his free transfer from Chelsea while former Blues boss Alan Little joins his brother Brian at Hull as a scout. Kevin Maher also signs a one-year contract while the 2001/2002 league fixtures give Blues a home game against Darlington on the opening day.