Pools were 2-0 up and cruising thanks to first half goals from debutant Tyler Hamilton and Ryan Donaldson either side of a Dimi Konstantopoulos penalty save from Jon Stead.
But a final 13-minute collapse from the visitors saw Harrogate progress as a Peter Kioso own goal pulled one back for the home side at the CNG Stadium before Konstantopoulos, on his second debut, dropped a high ball after being pushed as Connor Hall stroked it into an empty net with four minutes of normal time remaining.
And just when the game looked to be heading to extra-time, the Greek goalkeeper let the ball slip through his fingers as Brendan Kiernan pounced and walked the ball into the goal. Scroll down and click through the pages to see our player ratings from the match..
1. Dimi Konstantopoulos - 4
Made several good stops throughout the afternoon and looked to be enjoying a dream second debut when he saved Jon Stead’s first half penalty. But two calamitous spills late in the game ultimately cost Pools a place in the second round. Photo: HUFC
2. Kenton Richardson - 5
Busy in the first half and always keen to get forward. Switched off at points in the second as Harrogate turned the game on its head. Photo: Frank Reid
3. Peter Kioso - 5
Another own goal for the returning defender who was utilised as a centre-back as part of a shaky back four. Photo: Paul Paxford
4. Fraser Kerr - 4
A clumsy challenge gifted Harrogate a penalty which was thankfully saved but wasn’t convincing without Raynes alongside him. Struggled to deal with a bouncing ball in the build-up to Harrogate’s winner. Photo: Paul Paxford