Town were unable to reach the Emirates FA Cup Third Round for a second year running as their 2022/23 campaign came to an with a 3-1 defeat at Hartlepool.
The damage was done late in the first half when Callum Cooke opened the scoring, minutes before Joe Mattock was shown a yellow card while conceding a penalty that Josh Umerah converted.
Another from Umerah made it three, though Josh Coley's first goal in Town colours did provide one positive, it was too little too late to threaten the outcome of the tie.
Simon Weaver made one enforced change from last weekend's dominant victory over Mansfield as injured midfielder Matty Daly was replaced by fellow Huddersfield loanee Josh Austerfield.
Keith Curle made five changes to his Hartlepool side, including handing a debut to goalkeeper Alex Cairns who had signed earlier in the day on an emergency loan from Fleetwood.
Town had the first effort of the afternoon through Austerfield's high effort, but it was Pools who were on top in the opening exchanges with Josh Umerah and Jake Hastie going close, before Pete Jameson kept out Umerah's strike.
The chances slowed for the hosts, but Curle's side still took the lead in the 40th minute when Cooke's free kick proved too powerful for Jameson to keep out.
More damage was done to Town's cause deep into first half stoppage time as Mattock brought down Umerah from behind, conceding a penalty and being shown a second yellow card in the process.
Umerah confidently stepped up and stroked home to see his side two up at the break.
Despite being a man down, Town threatened early on in the second half with Danny Grant wanting a penalty after going to ground inside the box and Josh Falkingham seeing his edge of the box effort well held.
With Town having made all five changes, Hartlepool added a third through Umerah who was played in behind the Town defence and finished with power.
Harrogate found a response two minutes later though as a clever Sam Folarin dummy created space for Coley to claim his first Town goal.
Pools threatened a fourth late on with Jameson making a good save at the near post and Hastie firing wide as the contest ended 3-1 to the hosts.
Town: Jameson, Mattock, Falkingham (Frost 59), Burrell, Grant (Coley 66), Headley, Pattison (Thomson 45), Austerfield (McArdle 45+4), Muldoon (Folarin 66), Ramsay, Armstrong
Subs not used: Giles, Welch-Hayes, Richards, Horbury
Goals: Coley 73
Booked: Mattock, Headley, Coley
Sent off: Mattock
Hartlepool: Cairns, Ferguson, Hastie, Featherstone, Umerah (Hamilton 80), Cooke, Sylla, Menayese, Tumilty, Odour (Stephenson 74), Missoula (Grey 67)
Subs not used: Darcy, Kitching, Paterson, Taylor, McDonald, Ndjoli
Goals: Cooke 40, Umerah (p) 45+4, 71
Booked: Missoula, Umerah
Referee: Sam Purkiss
Attendance: 2,772 (294 away)