Blues suffered a 3-1 defeat to Gillingham at the MEMS Priestfield Stadium in a game that saw Southend finish the game with 10 men and Gills miss two penalties.
The home side dominated the first-half, forcing a string of saves out of Mark Oxley before breaking the deadlock just before the interval with a deflected Alfie Jones effort.
Stuart O’Keefe doubled Gillingham’s lead 40 seconds into the second-half but Simon Cox would fire Blues back into the contest with just over half an hour remaining.
Southend’s hopes of an equaliser looked dashed when substitute Emile Acquah received two yellows in two minutes to receive his marching orders.
Gillingham then had the chance to wrap things up with two penalties in quick succession, but after Mikael Ndjoli hit the post with his first effort, his second was saved brilliantly by Oxley.
Steve Evans’ side though would make the points safe late on as Oxley parried a shot into the reach of Brandon Hanlan who stabbed in Gillingham’s third to grab their first win in four.
Defeat for Blues was their ninth from their opening 11 games of the season and ended a run of three straight wins over their hosts prior to this afternoon.
Following last weekend’s reversal by Accrington, Caretaker boss Gary Waddock made two changes with Jason Demetriou and Isaac Hutchinson coming in for Sam Mantom and Brandon Goodship.
The home side got off to a really bright start and Blues goalkeeper Mark Oxley had to be on top of his game early on as Gillingham forced three saves out of the Southend stopper.
Oxley was made to tip a Mikael Ndjoli strike around the post at full-stretch before Brandon Hanlan stung the palms of Oxley with a near-post effort that was parried away.
Oliver Lee then tested out Oxley after being picked out by a low ball into the box by Alfie Jones, with the Hearts loanee firing a first-time effort on target but Oxley was equal to it.
Southend weathered the storm but were struggled to put pressure on the Gills backline with the home side continuing to create the clearer opportunities in front of goal.
Blues’ only chance in the opening 45 minutes came when Simon Cox slid Hutchinson in but Jack Bonham spread himself well to smother the young winger’s effort.
But within seconds of that chance up one end, Gillingham would go and break the deadlock up the other end as Alfie Jones fired in with two minutes of the half remaining.
Jones was picked out on the edge of the area before firing his half-volley goalwards, seeing his effort take a wicked deflection off Rob Kiernan to beat Oxley who got a hand to it but couldn’t keep it out.
The lead was arguably deserved by the home side and they could have grabbed a second before the break when Oliver Lee smashed the crossbar from close range in first-half stoppage time.
It wasn’t to matter though as Gills would double their lead 40 seconds after the restart as Lee laid the ball back to former Blue Stuart O’Keefe who curled the ball in from just inside the box.
Southend had won all of their last three meetings with Gillingham, but they were going to need something special to turn things around at Priestfield to extend that run to four.
And Blues would give themselves a glimmer of hope as they grabbed one back just before the hour mark as Cox halved the deficit with a well-taken effort.
Stephen McLaughlin played a free-kick from the left into the feet of the Southend striker who turned his man before firing through Bonham to put Southend back in the contest.
Cox’s effort lit a fire under Blues who looked a changed team with Stephen Humphrys and Elvis Bwomono both having efforts on goal blocked as the visitors pushed for an equaliser.
But much like last weekend against Accrington, Southend’s hopes were dealt a huge blow as they were reduced to 10 men as Emile Acquah was given his marching orders.
The sub, who’d only come on in the 55th minute, was booked for a clash with Connor Ogilvie before being given a second yellow card for a foul on Barry Fuller two minutes later.
Gillingham would immediately capitalise on having the extra man as Ndjoli won the home side a penalty, being brought down by Harry Lennon inside the penalty area.
The loanee from Bournemouth brushed himself down to take the penalty, but he missed the target, hitting the outside of Oxley’s right-hand post to keep Southend in it.
Gillingham though would earn a second bite of the cherry from the penalty spot as they won a second penalty but again Ndjoli was denied, this time by a fantastic save to his left by Oxley.
It looked as though the footballing gods were looking down on Blues who pressed for an unlikely equaliser, but any hope of that was ended when Gillingham grabbed a third for the home side.
Oxley pushed a shot from the left into the path of Hanlan who stretched out to prod the ball into the unguarded net and wrap up the points for Gillingham.
Gillingham XI: Bonham, O’Keefe, Ehmer (C), Ogilvie, Hanlan (Jakubiak 90+2’), Ndjoli, Fuller (Tucker 90+4’), Jones, Byrne, Lee (Marshall 65’), O’Connor. Subs Not Used: Walsh, Mandron, Charles-Cook, Pringle
Blues XI: Oxley, Bwomono, Milligan (C), Humphrys, Cox, McLaughlin, Kiernan, Hamilton, Demetriou (Shaughnessy 55’), Lennon, Hutchinson (Acquah 55’). Subs Not Used: Bishop, Hyam, Dieng, Ndukwu, Taylor
Referee: Leigh Doughty
Assistants: Stuart Butler & Samuel Ogles
Fourth Official: Daniel Cook
Gillingham: Alfie Jones 43’, Stuart O’Keefe 46’, Brandon Hanlan 87’
Southend United: Simon Cox 58’
Gillingham: Barry Fuller 57’
Southend United: Emile Acquah 63’, Harry Lennon 70’, Elvis Bwomono 71’
Southend United: Emile Acquah 65’
Attendance: 5,091 (704 Away Fans)