Premier Division champions Staithes will host rivals Staxton in the stand-out tie of Cayley Cup draws.
The winner of the clash will go on to meet the victors from the derby encounter between Cloughton and Scalby.
Relegated Mulgrave will need to beat the winner of the Great Habton v Wold Newton to progress in the Division One competition.
Kirkbymoorside, promoted to Division Two, play Sewerby 2nds in the last eight.
Scarborough Rugby Club host Snainton in the pick of the Division Three games, while newcomers Mulgrave 2nds play Muston 2nds in the Division Five competition.
Beckett League secretary Simon Dobson said: “The draw has brought us some fantastic ties across all divisions and I’m looking forward to the popular T20 format commencing in May.”
The Beckett League have also introduced a new finals day, which will see three of the competitions reach their conclusion on Sunday August 12 at North Marine Road, with a pink ball being used for these finals.
FULL CAYLEY CUP DRAW
A: Heslerton v Filey
B: Staithes v Staxton
C: Nawton Grange v Settrington
D: Cloughton v Scalby
Winner of D v Winner of B
Winner of A v Cayton
Forge Valley v Winner of C
Ebberston v Seamer.
A: Brompton v Flixton 2nds
B: Great Habton v Wold Newton
Winner of A v Thornton Dale
Winner of B v Mulgrave
Bridlington 2nds v Sherburn
Staxton 2nds v Wykeham.
A: Scalby 2nds v Ebberston 2nds
B: Wykeham 2nds v Fylingdales
Winner of B v Winner of A
Ravenscar v Scarborough 3rds
Kirkbymoorside v Sewerby 2nds
Cayton 2nds v Ganton
A: Scarborough RUFC v Snainton
B: Forge Valley 2nds v Cayton 3rds
Seamer 2nds v Flamborough
Nawton Grange 2nds v Pickering 3rds
Flixton 3rds v Winner of A
Muston v Winner of B.
A: Mulgrave 2nds v Muston 2nds
B: Heslerton 2nds v Thornton Dale 2nds
E: Wykeham 3rds v Scalby 3rds
F: Wold Newton 2nds v Ganton 2nds
G: Forge Valley 3rds v Filey 2nds
H: Cloughton 2nds v Sherburn 2nds
Scarborough Nomads v Winner of F
Winner of H v Winner of E
Ravenscar 2nds v Winner of A
Winner of B v Winner of G.