Chris Hargreaves' Torquay side have dropped to the foot of the Football League after a miserable run of five defeats and a draw in their previous six matches but they stunned Keith Hill's men at Plainmoor on Tuesday.
Krystian Pearce opened the scoring for the home side but Jamie Allen pegged them back before half-time.
Joss Labadie had the final say though, firing home from close range to give Torquay three precious points as they battle to pull off a great escape.
The victory leaves them seven points behind Devon rivals Exeter City, who sit just above the relegation zone.
Rochdale remain third in the table on the back of their first defeat in seven matches and Olly Lancashire was shown a red card two minutes from time to add insult to injury.
Exeter's alarming slide continued after they slumped to a fifth defeat in their last six games against fellow strugglers Northampton Town.
Northampton won 1-0 thanks to Ian Morris' second-half goal and are now unbeaten in five games.
Chesterfield remain a point clear of Scunthorpe United at the top of the table after the leaders were held to a 1-1 draw by AFC Wimbledon.
Paul Cook's side were beaten 3-1 at Accrington Stanley on Saturday and they must have feared another defeat when George Francomb put Wimbledon in front five minutes into the second half but Oliver Banks secured a point for Chesterfield five minutes later.
Scunthorpe looked set to take over at the top when they took a 2-0 lead over Southend United courtesy of goals from Matt Sparrow and Sam Winnall, but Phil Brown's side had other ideas as goals from John Egan and John White denied the home side.
Fourth-placed Burton Albion were held to a goalless draw at Portsmouth and Fleetwood Town also had to settle for a point, as they were held to a 2-2 draw at Lancashire rivals Bury, with Daniel Nardiello scoring both goals for David Flitcroft's side at Gigg Lane.
Oxford United failed to take advantage of dropped points from their fellow promotion contenders as they were held to a 1-1 draw by Cheltenham Town, Jamie Cureton denying them six minutes from time.
Conor Hourihane scored the only goal of the game as Plymouth Argyle won at Wycombe Wanderers to move level on points with seventh-placed Southend.
York City's charge towards the play-off places continued as they won 1-0 at Mansfield Town to stretch their unbeaten run to seven matches.
Morecambe hammered Newport County 4-1, Dagenham and Redbridge were 2-1 winners at Bristol Rovers, while Accrington Stanley and Hartlepool played out a goalless draw.
