Two red cards and two penalties ensured Town ended 2017 with a defeat after both Warren Burrell and Terry Kennedy were given their marching orders at Blackwell Meadows.
It took just eight minutes for the first spot kick to be awarded as Lloyd Kerry's late challenge on Stephen Thompson gave Reece Styche the chance to score from the spot.Styche made it two after 26 minutes bundling home from close range after a goal mouth scramble that saw both post and bar hit.
The introduction of Jack Emmett looked to prompt a comeback as the midfielder teed up Simon Ainge at the back post, though any recovery was cut short when Burrell was shown a straight red card for a sliding challenge.
Just three minutes later the hosts were awarded their second spot kick, and Town given their second red card as Kennedy pulled back Harvey Saunders allowing Thompson to score.
Simon Weaver made two changes from Saturday's 3-0 win over North Ferriby as Jack Vann and Simon Ainge replaced Ryan Fallowfield and Mark Beck.
After just eight minutes the hosts were awarded a spot kick after Stephen Thompson was challenged late by Lloyd Kerry inside the box, allowing Styche to step up and give his side the lead.
Dominic Collins had a clear chance to put his side two up five minutes later when he got on the end of Josh Gillies deep free kick, but headed over from closer range.
The hosts did get their second after 26 minutes when, after a goal mouth scramble that saw both post and bar hit, Styche bundled home his second of the afternoon from close range.
Just after the half hour mark, Terry Kennedy almost claimed his third goal in two matches after meeting Joe Leesley's cross, but heading onto the roof of the net.
The final chance of the first half fell to George Thomson after Leesley's crossed was tipped towards the winger by James Talbot, though Thomson's volley cleared the cross bar.
Kerry's deflected cross almost found the top corner minutes after the restart though Talbot managed to scramble the ball behind for a corner, that Ainge will be disappointed not to have turned into a goal after meeting Leesley's delivery at the back post.
The introduction of Jack Emmett and Jordan Thewlis looked to have breathed new life into Town, who were unlucky not to be awarded a penalty as Leesley went to ground under a challenge in the box.
Emmett then created Town's opening goal finding Ainge unmarked at the back post with a low cross that the striker gladly converted after 65 minutes.
Despite having the majority of the play, Town's comeback suffered a major blow in the 83rd minute when Burrell was shown a straight red card after carrying the ball out from defence, but going into a sliding challenge with too much force according to the referee.
Just two minutes later referee Paul Brown produced another straight red card for a man in blue, and pointed to the spot once again as Kennedy was given his marching orders for bringing down Harvey Saunders.
Thompson stepped up and found the top left corner to end Harrogate's hopes of a comeback and ensure the last fixture of 2017 would end in defeat.
Harrogate Town: Belshaw, Vann, Parker, Falkingham, Kennedy, Burrell, Thomson (Thewlis 60), Kerry (Emmett 58), Ainge, Agnew (Beck 81), Leesley
Subs not used: Cracknell, Swain
Goals: Ainge 65
Booked: Thomson
Sent off: Burrell, Kennedy
Darlington: Talbot, Collins, Scott, Turnbull, Heaton, Brown, Gillies, Wheatley (Glover 90), Styche (Saunders 57 (Mills 88)), Syers, Thompson
Subs not used: Marrs, Caton
Goals: Styche 8(p), 26, Thompson 85(p)
Booked: Turnbull, Glover
Referee: P Brown
Attendance: 1,759