Boro's Under-23s' North Riding Senior Cup quarter-final clash against Marske United will take place on Tuesday January 28 (7.45pm).
The last eight tie between the two sides is a rematch of last season's semi-final, where Marske prevailed to secure a place in the final against Scarborough.
Marske, last year's beaten finalists, will host the quarter-final tie at their home ground Mount Pleasant on Tuesday January 28 with a 7.45pm kick-off.
The young Boro side earned their place in the quarter-finals with a 4-1 victory over Boro Rangers.
Marske booked a last eight spot in the competition with a convincing 8-0 triumph against Northallerton Town.