The Spireites travel to Roots Hall this Saturday to face Southend in the 61st meeting between the two sides.
Chesterfield have come away with the victory on 24 occasions and we take a look at the last five times the Blues took all three points against the Shrimpers.
Southend United 0-1 Chesterfield: Saturday, March 5, 2016
Heading into the game, the hosts were chasing a League One play-off spot and Danny Wilson’s team were looking to steer away from the relegation zone.
Southend threatened Tommy Lee’s goal, but the fans’ favourite goalkeeper was on hand to deny David Worrall.
With time almost up, Ollie Banks slipped through Lee Novak and the striker kept his composure to take the three points back to Derbyshire.
The victory meant that the Spireites moved six points clear of the drop zone and took a huge step towards League One survival.
Chesterfield 3-0 Southend United: Tuesday, October 20, 2015
Novak scored an early opener to fire Chesterfield in front – rounding Daniel Bentley before slotting home into an empty net.
The lead was doubled just before the break when Sylvan Ebanks-Blake fired his effort into the top-right corner of the Southend goal.
Ebanks-Blake added a second goal to his tally just after the hour-mark; he bundled home Ian Evatt’s header from point-blank range.
The victory left the Spireites in ninth place after a goof start to the 2015/16 League One season.
Chesterfield 2-1 Southend United: Saturday, August 24, 2013
An early season clash at the Technique Stadium proved to be a highly entertaining game between two sides that spent the majority of the season towards the top of the table.
The Blues opened the scoring on the hour-mark when Gary Roberts curled his 25-yard free-kick into the back of the net.
The away side levelled nine minutes later after Freddy Eastwood swept home following a smart team move.
Armand Gnanduillet extended Chesterfield’s unbeaten start to the season when he scored an added time header to send the home fans into raptures.
Southend United 2-3 Chesterfield: Saturday, January 8, 2011
Danny Whitaker scored the opener after 12 minutes, slotting home a penalty after Jack Hunt was brought down by Craig Easton.
Deane Smalley doubled the lead seven minutes later when his long-range piledriver found the back of the net.
Easton halved the deficit moments before the hour-mark, but Whitaker restored the two-goal lead through another spot-kick.
Barry Corr won and scored a penalty late on to give Southend hope. However, John Sheridan’s side came away from Essex with a priceless away win.
Chesterfield 2-1 Southend: Saturday, October 9, 2010
Jack Lester won a penalty just before the half-hour-mark after being brought down by Graham Coughlan; Whitaker took responsibility and fired Chesterfield into the lead.
The Shrimpers were level less than ten minutes later when Anthony Grant fired his effort past the outstretched arm of Lee.
Scott Boden controlled and volleyed the ball home in added time to secure a dramatic win for the Spireites.
The win moved the Blues within a point of League Two leaders Port Vale and showed the resiliency of the side that season.