Despite a spirited second half performance, ten man Town fell to a narrow defeat on their first visit to league leaders Newport County.
Brandon Cooper headed home from a corner with just two minutes of the second half remaining to break Town hearts, after Simon Weaver's side had come from behind to almost earn a point in South Wales.
Padraig Amond had put his side ahead on the half hour mark, before Josh Falkingham was given his marching orders for a second half.
Town responded well to the setback with Will Smith getting his side back on level terms shortly after, but were ondone in the 88th minute with a towering header.
Weaver made four changes from Tuesday night with Aaron Martin and Lloyd Kerry both recovering from knocks picked up at Colchester.
Dan Jones came into the side for Ryan Fallowfield, who missed out due to being in self isolation after a family member tested positive for Covid-19.
After an early downpour in South Wales, Falkingham registered Town's first effort of the afternoon, volleying over after George Thomson's free kick was only half cleared.
James Belshaw was called into action in the 28th minute, springing to his left to keep out Amond who had peeled away to the left and tried finding the far corner.
County's number nine would get the break through two minutes later though after an incisive move by the league leaders.
Joss Labadie fed Liam Shephard in between Brendan Kiernan and Jones, with the County man then finding Amond with a perfectly weighted first time cross that his teammate gladly finished.
Town responded well to going behind, but were reduced to ten men eight minutes before the interval as Falkingham was shown a second yellow card for what the Referee deemed a dive in the Newport area.
The ten men of Town would equaliser before the half was done though, Jones rising highest to meet Thomson's corner and nod the ball in the direction of Jack Muldoon, with Smith applying the final touch from under the cross bar.
Town didn't let the numerical disadvantage affect their play early in the second half, with the Exiles forced into making a change in formation and moving to a four at the back.
It was Town who had the ball in the net next, though it wouldn't stand after Martin had bundled past Nick Townsend from another dangerous Thomson delivery.
Thomson then had Town's best chance of the second half after Muldoon had wriggled into the area and cut the ball back, but the midfielder could only find the side netting with his finish.
County were being limited to long range efforts and crosses into the box, though got the decisive breakthrough with just two minutes to go, Cooper heading home from close range after a corner was swung over Belshaw to the far post.
Despite Connor Hall being sent forward as an emergency centre forward, County held on in the dying stages and send Town home with nothing to show for their efforts.
Harrogate Town: Belshaw, Jones, Falkingham, Smith, Burrell, Thomson, Martin (Beck 85), Kiernan (Kirby 40), Kerry, Muldoon, Hall
Subs not used: Cracknell, Stead, Walker, Lokko
Goals: Smith 43
Booked: Kerry, Falkingham, Jones
Sent off: Falkingham
Newport County: Townsend, Haynes, Labadie, Cooper, Bennett (Devitt 81), Amond, Sheehan, Abrahams (Willmott 60), Twine, Demetriou, Shephard (Proctor 60)
Subs not used: King, Baker, Webb, Ellison
Goals: Amond 30, Cooper 88
Referee: P Howard