Jon Stead scored his first two Town goals before being dismissed with a second yellow card in what proved to be the pivotal moment in a 4-2 defeat at Torquay.
The striker struck from the spot to give Town a half time lead, before striking again to restore the advantage after Jake Andrews had equalised.
Just minutes later though Stead was dismissed for a second yellow card, with goals from Kalvin Lumbombo-Kalala and Jamie Reid turning the tie in Torquay's favour.
Reid added his second ten minutes from time to end any hope of a Town comeback and send Simon Weaver's side on a long journey back empty handed.
Weaver made one change from Tuesday night's victory over Chorley as Jack Emmett replaced the injured Josh Falkingham, with Warren Burrell taking the Captain's armband.
With the home fans behind them, Torquay looked to grab an early goal, but were prevented any real sight until the 14 minute mark when Frank Vincent sent a low shot flashing across goal.
The hosts struck the woodwork seven minutes later as Robbie Cundy climbed highest from a corner, but saw his effort bounce back off the upright.
Town soon began to threaten themselves though, as Scott Brown brought Lucas Covolan Cavagnari into action with a snap shot from 25 yards.
With 33 minutes played, Town were awarded a penalty when Brendan Kiernan's through ball found Stead, who was then brought to ground inside the area.
The striker picked up the ball and sent the 'keeper the wrong way from the spot to send his side into the break ahead with his first Town goal.
The lead lasted just six minutes into the second half though as good work from substitute Kalvin Lumbombo-Kalala led to a low cross coming in from the right, that Andrews dispatched.
Stead popped up again though in the 58th minute to put Town back in the lead, converting George Smith's deep cross with a sliding finish.
Just five minutes later though and Town's number 16 was given his marching orders, picking up a second yellow card for handball despite it looking to come off his shoulder, that meant Town had to see out the remaining 27 minutes with ten-men.
The hosts tried to make their numerical advantage pay, but James Belshaw kept out Reid's effort with a good reaction save, minutes after Stead's dismissal.
The red card proved costly as Kalala took aim from 30-yards and sent a swirling shot past Belshaw to level the score with 21 minutes to go.
Three minutes later and Torquay were ahead as Reid beat Belshaw from the spot, albeit at the second attempt, after Will Smith had brought down Andrews.
Any hopes of a comeback for ten man Town were put to bed in the 80th minute as Reid claimed his second goal and sealed the points, firing past Belshaw from close range.
Harrogate Town: Belshaw, Fallowfield, G Smith, Burrell, Emmett (Beck 65), Kiernan (Jones 75), Stead, Muldoon, Hall, Brown, W Smith
Subs not used: Thomson, Cracknell, Diamond
Goals: Stead 33 (p), 58
Torquay: Cavagnari, Wynter, Davis, Cameron, Lewis (Dickson 66), Duku (Lumbombo-Kalala 45), Andrews (Buse 86), Vincent, Reid, Cundy, Whitfield
Subs not used: MacDonald, Slough
Goals: Andrews 51, Lumbombo-Kalala 69, Reid 73 (p), 80
Booked: Davis, Vincent
Referee: A Jackson
Attendance: 2,527 (59 away)