A Town side made up of mostly U23s lost out on a place in the West Riding County Cup Final as Guiseley Captain Jamie Spencer headed home the winner three minutes from time at The CNG Stadium.
Josh Hardcastle became the first player from Town's U19 Alliance team to start a first team fixture, alongside first teamers Joe Cracknell, Alex Bradley and Kian Harratt.
There were places on the bench for Hardcastle's U19s teammate Lewis Thornton and U17s defender Harry Lee, while the visitors named a side featuring plenty of regular first team names.
Cracknell was the star of the first 45, producing two saves of the highest quality to first deny Christopher Sang, then Kennedy Digie's header to keep it goalless going into half time.
The strike partnership of Harratt and Aaron Haswell went closest for Town, but neither could find the corner with their efforts.
Aaron Haswell had an effort ruled out for an earlier offside in the 52nd minute, before Another brilliant piece of goalkeeping kept the visitors out, Cracknell denying Jamie Spencer and Sang with a double save.
Town failed to clear their lines though, fouling Kennedy Digie and giving Gabriel Johnson the chance to open the scoring from 12 yards, a chance he did not waste.
The lead lasted just eight minutes though as Josh Wicks unlocked the pace of Harratt with a well weighted through ball, with the striker then able to beat Bradley Wade with a right footed finish.
Cracknell's heroics continued with more outstanding saves, but in the end the experienced Guiseley side found a winner, Captain Jamie Spencer heading home from a corner in the 87th minute to seal The Lions' place in the final.
Harrogate Town: Cracknell, Hardcastle, Chippendale, Bradley, Hartley, Clark, Wicks, Robinson, Haswell, Harratt, Prata (Crook 69)
Subs not used: Lee, Foster, Hutton, Thornton, Katsamagkas
Goals: Harratt 72
Guiseley: Wade, McNally, Nicholson, Smith, Digie, Ekpolo, Sheppeard, Spencer, Sang, Soleman, Johnson
Subs not used: Cantrill, Wilkinson, Fox, Clayton, Ferreira
Goals: Johnson 64 (p), Spencer 87
Referee: S Barrott