Filey Town won 4-2 on penalties after extra-time at top-flight rivals Newlands in the Scarborough Saturday League Cup.
Town took an early lead with young debutant Harry Ward notching after only five minutes, but Liam Mancrief levelled to make the score 1-1 at the interval.
Dan Freer fired the home side in front midway through the second half before Jack South levelled for Filey.
There were no further goals before the 90-minute mark, and the scores remained locked at 2-2 after extra-time so the match went to penalties.
Town keeper Jonny Hunter was the shoot-out star, saving two Newlands penalties, with Nathan Vernon, Harry Keary, South and Ward all on target in a 4-2 shoot-out success.
Man of the match for Filey was Max Gage, with Lee Lambert and Josh Westmorland impressing, while Jack Hakings was the man of the match for Newlands.
Snainton battled hard to claim an extra-time 4-3 win in a thrilling cup-tie at Eastfield Town.
The villagers ran the game in the first half, going 2-0 ahead after 35 minutes, Town pulling a goal back five minutes before the break.
The visitors created a string of chances after the interval, but failed to take them and Eastfield levelled from the penalty spot.
A goal apiece from either team in a frantic finale made it 3-3 after 90 minutes so the game went to extra-time, Snainton finally edging home in the added 30 minutes.
Zac Hansen scored twice for Snainton with Dylan Muggeson-Forbes and man of the match Rob Holt also notching.
Edgehill also moved through to the next round with a 4-1 home win against Hunmanby United.
Jimmy Beadle scored twice from the penalty spot for Edgehill, with Sean Exley scoring the other two for the home side.
James Pinder notched a late goal for United, whose man of the match was John Emmerson.
Man of the match for Edgehill was central midfielder Ryan Link, who was pushed close by youngster Robbie Scarborough.