And the Shrimpers are becoming very good at doing just this, for the second time in six days.
Blues boss Paul Sturrock made four changes to his starting line-up of which it was great to see striker Matt Paterson given a surprise recall upfront.
Blair Sturrock drops to the bench joining wideboy Louie Soares who is replaced on the right by new signing Miguel Comminges for his full debut.
Rhys Evans poor first five minutes against Cheltenham Monday sees Glenn Morris back between the sticks, and Anthony Grant in central midfield for the boy Kane Ferdinand, both becoming subs as well.
The league's top team had already shown the Roots Hall faithful that they meant business when the Spireites skipper Dwayne Morris found himself clear on the Southend goal but he decided to shoot from 16 yards out and it was well saved by the returning Morris.
So at least we weren't two down after five minutes, it took 19 this time around!
Jack Hunt being brought down by Shrimpers skipper Craig Easton, an awful tackle considering they were in the 12-yard area, and Danny Whitaker slotted the spot-kick low into the centre of the goal for this 10th goal of the season, repeating his effort from the first game between the sides back in October.
After the hard-working Ryan Hall had at least forced a save from Chesterfield keeper Tommy Lee, it was the away side that doubled the advantage in the eight minutes later, with some poor defending.
Southend were trying to find a way through the uncompromising league leaders defence after a free-kick, when Whitaker's clearance released Dean Smalley and he raced upfield, left-back Johnny Herd made a huge misjudgement and went on to fire past a diving Morris for his second goal of the campaign on his first full league start!
There was little seen from the home attack and as hard as Corr and Paterson tried a Grant shot was the best United could muster before the referee thankfully blew for half-time, and a welcome bottle of Bulmers, at £3 a go, not bad, eases the pain better than a cup of Bovril!
Debut boy Miguel Comminges was replaced by Kane Ferdinand and obviously needs some game time, he was very poor here, but very early days.
Southend reduced the arrears in the 58th minute with a absolute cracker. Herd's long throw was cleared as far as Craig Easton and the midfielder unleashed a curling 25-yard right-footed shot into the top right corner.
The Blues were back in the game, for four minutes!
That's all it took for Chesterfield to restore their two-goal advantage when Ryan Hall, what was he doing, caught Drew Talbot in the box, and upstepped Whitaker to fire home the spot-kick into the bottom right corner beyond Morris' reach.
There then followed the traditional Shrimpers pressure late on when two goals down, and eventually pulling one back too late, first with Lee saving well but his parry out found Hall at the back post whose goal bound effort was put behind for a corner by Spireites right back Hunt.
Then Referee Roger East awarded the game's third penalty and one to the home side at last when Derek Niven pulled down Barry Corr, who got up and smashed the ball into the top left hand corner for his 11th goal of the season and his third of the trot, any watching scouts, possibily one from Crawley Town, would be making notes.
Could the Blues do it this time and grab a point? No.
Still, at least next week we're back on our travels, and it can't get harder than the division's first placed side, so roll up second placed Rotherham, easy.
And having horribily misquoted Jane Austen at the start of this piece, I'll end on her exact words, Austen in a footy report, it's class on this site, so for those who want changes at the top, we didn't play that badly, and two games ago were coming off back-to-back 2-0 away wins, I say, or she said: 'Angry people are not always wise.'
Southend Player Markings: Morris - 6, Clohessy 6, Barker 6, Coughlan 6, Herd 5, Comminges 4 (Ferdinand - 6), Easton 6, Grant 5, Hall 7, Corr 6, Paterson 6 (Sturrock 80).
Referee: Mr. R. East - 7.
Shrimpers 2-3 Spireites: View commentary, squad, and statictics of the game as it happened.