Pools found themselves behind inside five minutes when Rushian Hepburn-Murphy drilled in a fine goal from distance to open the scoring.
The Robins looked the side likely to add to the scoreboard with Pools out of sorts in comparison to what we have seen under Askey so far since his arrival at the Suit Direct Stadium.
But Hartlepool were able to hang in the game which would ultimately provide them with the platform to secure all three points.
Connor Jennings swept home his third goal in four games at the Suit Direct Stadium to level things two minutes from time.
The referee confirmed eight minutes of stoppage time which gave Pools incentive to seek a winner which they would find through Oliver Finney when he found the bottom corner in the 94th minute to spark wild celebrations.
And here is how Pools were rated:
13. Wes McDonald - 7
Another tidy cameo from the winger. Gave Hutton something to think about and provided the assist for Jennings. Certainly a good option from the bench in this mood. (Photo: Mark Fletcher | MI News) Photo: Mark Fletcher
14. Tom Crawford - NA
Good to see him back involved. Brought on for his first appearance since October for the closing stages. (Photo: Chris Donnelly | MI News) Photo: Chris Donnelly
15. Oliver Finney - NA
Only featured for around eight minutes but how significant could they be? Added some energy to Pools before taking things on himself to fire in the second. Brilliant goal to spark wonderful scenes. Match winner. (Photo: Mark Fletcher | MI News) Photo: Mark Fletcher