Despite that, progression has been made by Blues this season under manager Phil Brown, in his first full season as Southend United boss.
Here, we take a look at how Blues got on in January, with cup games against Championship and Premier League opponents.
Southend United 2-1 Portsmouth
After ending 2013 with a point, Southend United began the new year with all three as they once again came from behind to beat Portsmouth.
Sonny Bradley gave the visitors the lead on the half-hour mark, but on the stroke of half-time, Ryan Leonard levelled with a deflected strike.
In tough conditions, both sides went in search of a winner, but it was Leonard who once again produced the goods.
The young midfielder was teed up by Barry Corr, and he executed a stunning low drive from 25-yards to win it for Blues in the final minute of the game.
Southend United 4-1 Millwall
As Championship side Millwall rolled into town, few could have predicted the events that would unfold in this classic FA Cup third round tie.
In horrible conditions at Roots Hall, Barry Corr handed Blues the lead with a well taken header from John White’s cross.
A floodlight failure stopped play for 15 minutes before Millwall were reduced to ten men when Jermaine Easter was sent off.
Will Atkinson doubled Blues’ advantage on the stroke of half-time, before Michael Timlin made it 3-0 early in the second-half.
Martyn Woolford pulled one back just after the hour mark for Millwall, under the guidance of caretaker manager, Neil Harris, a former Blues striker.
Phil Brown’s side however were not going to let the Lions back into it, and Ryan Leonard rounded off a comprehensive win against the side two leagues above Blues.
Plymouth Argyle 1-1 Southend United
Blues had lost just once since the start of November as they headed to Home Park to take on Plymouth Argyle.
In the absence of John White, Ryan Leonard wore the captain’s armband against his former club, but played at right-back.
Both sides had chances during an open game, but it was Plymouth who took the lead, as Dominic Blizzard’s shot deflected up and over Daniel Bentley.
Blues responded excellently, as Cauley Woodrow teed up Kevan Hurst to make it 1-1, and that’s how it stayed.
Southend United 3-0 Chesterfield
Blues produced one of their best performances at Roots Hall of the campaign as they geared up for their FA Cup fourth round tie.
Kevan Hurst opened the scoring, as a terrific ball from Luke O’Neill picked out Anthony Straker who squared it for Blues’ opposite winger to make it 1-0.
Ryan Leonard made it 2-0 with a terrific breakaway goal involving the midfield trio of Leonard, Will Atkinson and Michael Timlin.
Moments later and it was 3-0 as Adam Thompson’s long ball over the top found Barry Corr who expertly clipped the ball over Tommy Lee.
Blues’ clean sheet record was ensured when Daniel Bentley saved Marc Richards’ penalty.
Southend United 0-2 Hull City
Southend United’s first fourth round tie since 2008 ended in defeat, but they went out valiantly, as they were beaten 2-0 by Premier League side Hull City.
Barry Corr had a header saved brilliantly by Steve Harper, as Blues looked to shock the Tigers.
Michael Timlin then rattled a shot against the crossbar early in the second-half.
Blues’ failure to take one of those chances came back to haunt them when Matty Fryatt made it 1-0.
The striker then rounded things off late on with a second, but Blues had put up some fight against Steve Bruce’s side.
Dagenham & Redbridge 1-1 Southend United
Just three days after their FA Cup exploits, Blues were back in league action, and picked up a point at local rivals Dagenham & Redbridge.
After a goalless first half, another deflected strike away from home put Blues on the back foot, as Luke Norris’ striker looped up and over Daniel Bentley.
Blues once again responded well on the road as Kevan Hurst’s shot found its way into the bottom corner.
Adam Thompson could have won a penalty for Blues late on, but the game ended level.
Southend United 0-0 Newport County
Southend United made it two draws in a row, as they were held to a goalless draw by Newport County at Roots Hall.
Conditions at Roots Hall were terrible, and made it hard for either side to get the ball down and play any football.
The only real chance of the game came from the penalty spot, but Newport’s Robbie Willmot blasted widely over the bar.
Lee Barnard made his first appearance at Roots Hall since returning on loan from Southampton.