Playing their first match under new floodlights at home since 1962, Southport looked to have marked the occasion with a win but instead they were left to rue frustratingly familiar problems.
Substitute Craig Mahon scored a dramatic 84th-minute winner as Chester came from behind to earn maximum points at the Merseyrail Community Stadium.
Trailing to Louis Almond’s first-half opener, the visitors had shown little sign of a comeback until Michael Kay equalised to trigger a five-minute turnaround.
The victory is much-needed for Steve Burr’s team, who came into this match on the back of four defeats from their previous five matches.
But the result does nothing to help Southpot’s predicament at the foot of the Vanarama National League, as they sit third from bottom still with only two wins to their name all season.
Chester, deploying a new shape of 3-5-2 for the first time this season, did much of the early running but lacked any cutting edge.
The visitors created early chances as Jordan Chapell shot wide, so too did Johnny Hunt, the left wing-back, who bent an effort past the far post after cutting in from out wide. John Rooney also had a low shot saved by Port goalkeeper Andy Coughlin.
Southport, for the most part, were restricted to half-chances through Louis Almond and Cole Stockton. Mike Phenix sent in an excellent low cross from the right but goalkeeper Jon Worsnop intervened before it reached the unmarked Almond, lingering at the far post.
And it was Southport’s wide men who combined to excellent effect for the opening goal on 36 minutes. Phenix again made good ground on the right before playing the ball into the centre to Almond, who set himself before steering a stylish finish past the dive of the outstretched Worsnop from 19 yards.
In a half when quality was difficult to come by, it was a rare moment of individual excellence from the Southport attacker.
Phenix had Worsnop anxiously back-peddling with a deep cross which almost looped in from out wide, while Almond shot went close after half-time, latching onto a clearance from Ian Sharps.
Although Chester saw plenty of the ball in the second period, their play was disjointed and there was little indication that an equaliser would follow.
But with 11 minutes remaining, the visitors did level, Kay profiting from a mistake from keeper Coughlin, who came but failed to punch clear a Rooney corner, mopping up the loose ball.
And that provided Chester with the shot in the arm they needed, substitute Mahon plundering the winner after his shot from inside the area was fumbled in by Coughlin who was again culpable.
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