Gillingham's bad run of form continued on Monday night in front of the Sky TV cameras as Southend took all three points at MEMS Priestfield with a 2-1 win.
Liam Dickinson and Joe Martin's own goal gave the visitors a comfortable lead at the interval, and despite a late Gavin Tomlin effort the Gills couldn't get back on level terms and lost their third home League game of the season - their second in succession.
With the last two games having been postponed due to the weather, manager Andy Hessenthaler was hoping that the extended break would help his side break a run of four games without a win.
He was forced into three changes for the match with Charlie Lee and Jack Payne (who took a place on the bench) both struggling with ankle problems, so Matt Lawrence and Curtis Weston came in as replacements.
Paulo Gazzaniga made his first league start, replacing Ross Flitney who has recently had surgery on a knee injury.
Southend made four changes to the team that lost against Rotherham - Kane Ferdinand earning a place in the starting line-up having not featured on Friday evening.
The opening exchanges were fairly quiet with both sides enjoying decent possession, but nothing clear cut was offered in the first few minutes.
However Dickinson opened the scoring with Southend's first effort on 10 minutes when his left-foot strike inside the area gave Gazzaniga no chance in goal as the defence failed to clear their lines.
The goal came when Sean Clohessy's cross found an unmarked Ferdinand in the box and headed on for Dickinson, who got in behind Garry Richards and fired home.
It was the striker's 12th goal of the season and meant the Gills would have to come from behind if they were to register their first win since January 2.
But it was Southend who continued to press and Gazzaniga was forced into a fine save when Bilel Mohsni fired a shot from 25 yards.
A 25th-minute shot from Lewis Montrose from all of 25 yards was Gillingham's best chance in the first half an hour, summing up how difficult they were finding it to penetrate the visiting defence.
And six minutes later the deficit was doubled when David Martin beat the offside trap and fired a low cross in towards Ferdinand, and despite the presence of Andy Frampton and Martin, the ball found its way past Gazzaniga and into the net, with Martin appearing to get the final touch.
On 38 minutes the Gills finally came to life with Danny Jackman delivering a couple of excellent crosses into the box, but the Southend defence stood firm and resisted the pressure as the half-time interval approached.
The hosts made two substitutions at half time to freshen things up - Payne and Jack Evans coming on to replace Montrose and Lawrence.
However they were unable to make an impact early on as the Gills began the half in the same way the ended the first, in disappointing fashion.
Danny Kedwell was consistent throughout as he continuously won headers and flick-ons, but neither Tomlin nor Jo Kuffour were on hand to convert any resulting half chances.
In the 66th minute Tomlin had an opportunity to reduce the arrears, but with defenders surrounding his every move inside the box he could only shoot straight at Glenn Morris, who saved comfortably with his first real action of the evening.
The Gills' night got even worse on 77 minutes when skipper Frampton was forced off with an ankle injury, falling awkwardly as he went for a header, Connor Essam coming on to replace him and make his first-team debut.
There was a glimmer of hope for the home side four minutes from time when they reduced the arrears in some style.
The move started with Gazzaniga coolly passing to Evans, whose long ball found Weston. The midfielder touched into the path of Tomlin, and the on-loan Dagenham man did the rest, beating three defenders before lashing an unstoppable shot past Morris.
Despite throwing everything forward and a half chance for Weston, the hosts couldn't find the equalizer and Paul Sturrock's side took home all three points.
Gills: Gazzaniga, Lawrence (Evans 45), Frampton (Essam 77), Richards, Martin, Montrose (J Payne 45), Weston, Jackman, Tomlin, Kedwell, Kuffour.
Unusued subs: Hawkes, Whelpdale.
Southend: Morris, Clohessy, Mohsni, Timlin, Ferdinand, Martin (Hall 67), Phillips, Prosser, Kalala, Dickinson (Sampson 85), Barker.
Unused subs: Gilbert, Grant, Harris.
Referee: R East
Attendance: 4,441 (393 Southend)