Rivals Edgehill and Newlands will play each other in the North Riding County FA Saturday Challenge Cup.
Saturday Challenge Cup draw:
Edgehill v Newlands, Old Victoria v Itis Itis Rovers, Unicorn v West Pier, Seamer v The Raj.
Ties to be played October 7.
Sunday League Division One title challengers Angel and Newlands both face away trips in the Sunday Challenge Cup.
Angel travel to Riverside and Newlands are on the road at Village Park Rangers.
Holders Trafalgar are at home to Sunday League newcomers Valley.
Sunday Challenge Cup draw:
Riverside v Angel, Village Park Rangers v Newlands, Trafalgar v Valley, Brotton Railway Arms v Roscoes Bar, Golden Last v Ayton Reserves.
Ties to be played October 8.