In a terrific advertisement for Northern Premier League football, Whitby were denied at the death by the lively Marcus Dinanga as their December jinx continues.
The Seasiders drop to fourth in a tight top half going into Christmas, despite leading with a first-half Adam Gell strike.
Whitby boss Chris Hardy made two changes as Dave McTiernan and Callum Martin replaced Mikey Roberts and Connor Smith, who returned to parent club Hartlepool United.
Skipper Steven Snaith, pushed up front, forced Phil Barnes to parry early on with a powerful effort from distance. The Derbyshire hosts then had a purple patch as captain Joe Doyle-Charles forced Shane Bland to claw away from the top-right corner, on 19 minutes.
Seconds later, Marc Newsham backheeled for Niall McManus to sidefoot wide from a glorious position. Bland then caught Newsham's rising header.
Jamie Yates powered inches over before the Seasiders lead on the half hour. Martin's deep right-wing cross was cut back from the byline by Dale Hopson for Gell to turn home point-blank.
The visitors could and should have sealed things, on the hour, when Matty Tymon laid off from a great position, 12 yards out and McTiernan rounded Barnes, only for Nico Degirolamo to head off the goal-line.
Fifteen minutes from time, the lively Ted Cribley pulled back from the left and fellow sub Alex Pursehouse placed into the bottom-left corner from the right-edge of the penalty area.
The Gladiators were lifted but almost fell behind again when Dan McWilliams' curling free-kick was met with a diving Luke Bythway header for Snaith to turn in, only for the nodded assist to be flagged offside.
Hopson sidefooted wide from the edge of the box, for Whitby, Bland parried Mike Williams' low effort from distance and it was the home side's turn to have a scramble effort to be chalked off when Newsham was ruled offside.
However, the pressure continued and neat interplay saw Dinanga find space and slot into the same bottom-left corner for another heartbreaking late winner.
Other results broadly went in the Seasiders' favour, though leaders Rushall's own late 2-1 win at Skelmersdale saw them extend their lead over Town to seven points, while Boxing Day opponents Blyth go to the Turnbull ahead of Whitby on goal difference, in third, after a 2-0 victory over Barwell.