Kairo Mitchell and Charlie Carter returned to haunt their former club to put Eastleigh in control by half-time.
But a brilliant brace from Ryan Colclough and a 95th minute stunner from Andrew Dallas gave Paul Cook's side a famous victory.
"To get that last minute goal was fantastic for all of us," said Cook's Spireites assistant manager Danny Webb.
"I wouldn't say we were lucky to win because we deserved it. When you are 2-0 down at home, the very worst you take is a point. At 2-2 with five minutes left, you just felt that we were going to win the game."
Eastleigh were in front inside ten minutes when ex-Spireite Mitchell capitalised on carnage in the penalty area to stroke the ball into the back of the net from close-range.
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