Ayton moved into the League Cup quarter-finals after battling back from being behind on several occasions to win 3-0 on penalties after holding second division leaders Snainton 5-5.
The hosts took a 2-0 lead after 15 minutes through a Ryan Collings brace, defensive errors proving costly for Ayton yet again.
Sean Pinder's side gave themselves hope when Ian Laing tapped in a rebound when James Cooke's powerful free-kick was parried by the Snainton goalkeeper.
Regan Hewitt restored Snainton's two-goal lead, but a cracking solo goal from teenager Tom Varey, which saw him race past several home players before cutting in and firing home.
A towering header from Joe Bradshaw levelled for Ayton, but this did not last long as Damien Foster took advantage of some more lax defending from the visitors.
Ayton levelled yet again when defender Jaymaine White's huge clearance was headed over his own keeper by a home defender, but yet again Snainton regained their lead almost immediately through Connor Bell.
The away side refused to submit and forced the penalty shoot-out thanks to a second superb header from Bradshaw.
In the shoot-out., Ayton keeper Alex Glass saved the first three spot-kicks, while Cooke, player-boss Pinder - who brought himself on in the closing moments in order to take a penalty - and youngster Tyler Beck all hit the target as Ayton moved into the last eight.
Man of the match for Snainton was two-goal hero Collings, while Glass and Bradshaw shared the plaudits for Ayton.
Division One leaders Edgehill had to dig deep for their 2-1 win at second division title-chasers Itis Itis Rovers.
Lloyd Henderson put the top-flight side ahead on 20 minutes with a spectacular half-volley from 20 yards out.
Callum Myers came on at half-time for the hosts and within five minutes he poked the ball home after good play from Sam Pickard to make it 1-1.
Edgehill regained the lead on 70 minutes through Henderson's neat finish after a goalmouth scramble, and that was enough for the away side to move into the quarters.
The Edgehill boss Steve Clegg was quick to praise Rovers, he said: "They worked hard throughout the cup-tie, and while we never got into top gear we are in the next round.
"We have had some games in last few weeks where we have won easily and not been challenged so that's not the ideal preparation for a cup game like this, but we did enough.
"Our central midfielders Jamie Patterson and Joe Gallagher were our men of the match."
Rovers player-manager Mikey Barker said: "I am very proud of my lads as they played very well against the top team in the league.
"These are the kind of games we want to be playing in next season. In the second half I hit the bar with a shot, Curtis Rose hit the post with a header and Tom Sutherland missed when well-placed so we did well.
"I am proud of the lads, with left-back Neil Forsyth and centre-half Curtis Rose our star men."
Another thrilling cup-tie saw FC Rosette fight back from 2-0 down to win 3-2 at second division rivals Falsgrave Athletic.
A Travis Wood double put Falsgrave in charge early doors, the second a superb effort which saw the forward score with a long-range lob despite having his back to goal.
JP Watson then levelled the scores before the interval with two well-taken volleys, the second coming after a fine header back from Joe Logan.
On the hour mark Wood had the ideal chance to restore Athletic's lead from the penalty spot but a top save from Mikey Harland kept it at 2-2.
Ten minutes from time Rosette booked their place in the last eight when Dean Brierley chested the ball in from close-range after a corner sparked a goalmouth scramble.
Harland and central midfielder Watson shared the man of the match award for Rosette, while the Falsgrave star man was Shem Atkinson.
Newlands striker Stew Bates was the hat-trick hero as his side moved through with a 3-1 win at top-flight rivals Filey Town.
The visitors opened the scoring on 30 minutes when a foul on Dan Freer saw them awarded a penalty, which Bates converted.
Town were then awarded a penalty, which Tom Micklethwaite fired home to make it 1-1, but parity was short-lived as Bates restored Newlands' lead with a breakaway goal.
Filey started strongly in the opening 15 minutes of the second half but failed to turn their possession into goals and Bates made them pay, completing his hat-trick on the hour mark with a cracking finish.
Newlands boss Joe Hakings was happy with his side's all-round effort but singled out Bates for his hat-trick, while Town player-manager Jordan Philliskirk was left frustrated by his side's cup display.
Scalby eased to an 8-2 home win against Old Vic, despite the visitors battling back to make it 2-2 at one stage in the second half.
Carl Townley opened the scoring for Sam Medd's side on 10 minutes, and a Danny Wedge header made it 2-0 before half-time.
Vic pulled a goal back in the first minute of the second half with a stunning 20-yard strike, and the second division strugglers then levelled to stun Scalby.
The hosts roared back into life shortly afterwards, Carl Townley hitting his second to make it 3-2, Craig Rackham adding a fourth, with a Rob Speight double and goals from Nic Wheatman and Ashley Townley completing the win.
Central midfielder Carl Townley was the Scalby man of the match while the whole Old Vic team shared their star man award.
West Pier were handed victory as their opponents Ayton Reserves could not raise a team for their fixture.
In the Scarborough FA Junior Cup, Edgehill 3rds' game at home to Lealholm was abandoned on 70 minutes due to an injury to the referee.
Martyn Jenkinson had put Edgehill ahead in the first half, the visitors levelling midway through the second period, just a few moments before the match official suffered a calf injury that forced him off the pitch and caused the abandonment of the match.
Filey Town Reserves suffered a 3-1 home defeat to Beckett League outfit Heslerton in the ERCFA Junior Country Cup second round.
Paul Downes (2) and Dave Thompson were on target for Heslerton, whose men of the match were Curt Dickinson and James Webb.
Joe Gage scored Town's only goal.