A youthful City under-18s side - containing just four second-year scholars - was beaten 1-0 by Mansfield Town in their opening EFL Youth Alliance North East fixture of the season.
Nathan Caine's first-half penalty ensured Mark Trueman's 10 men left the fixture at the club's Woodhouse Grove training base empty handed.
The young Bantams began the encounter brightly, creating opportunities and testing the Stags' backline.
Nevertheless, despite showing promising attacking signs, City proved unable to keep their visitors at bay, with Caine converting from the spot after 17 minutes.
Three minutes later and Harrop was then given his marching orders, after - as the final defender - bringing a Mansfield attacker down on the edge of the area.
After this game-changing incident, Trueman’s young Bantams tried to hurt the away side on the counter attack and, in doing so, created opportunities through first-year scholars Cole Roberts and Raj Palit.
City pushed for an equaliser towards the closing stages but proved unable to convert as the Nottinghamshire outfit took all three points.
CITY: Tom Donaghy; Oliver Norman, Leke Ajibode, Charlie Wood ©, Luke Harrop (dismissed 20’); Tanaka Maumbe, Cole Roberts, Harvey Omerod, Dylan Youmbi; Raj Palit, Bobby Pointon. Subs (not used): Darryl Ombang (GK), Yahahan Tunkara, Noah Wandsworth, Sam Bentley, Freddie Jeffries.