Second division Fylingdales Reserves pulled off a shock 4-2 success at top-flight Itis Itis United in the Kenward Cup, while Commercial and Heslerton needed penalties to beat second division opponents Newlands Reserves and Cayton.
Lewis Peel gave the youthful visitors the lead and Dan Richardson soon doubled this lead to leave James Prethero’s team chasing the game in the first half.
United gave themselves hope with a Zac Hansen strike before half-time and when Chris Hannam levelled on the hour mark it looked like the hosts would secure the win.
But a Fylingdales Reserves side which included two 16-year-olds and five 17-year-olds, refused to submit and restored their lead through Zac Estill, and Dan Smith confirmed their place in the next round.
Keeper Dave Smith was the man of the match for the villagers while James Young was the star man for United.
Commercial keeper Ash Buck was the hero as his side won a dramatic encounter at home to second division strugglers Newlands Reserves 4-3 on penalties after the scores had been tied on 3-3 after extra-time.
Buck saved four spot-kicks and scored the winner in a shoot-out where both sides missed four of their first five penalties.
For Commercial, Joe Bayes missed, then Stu Wallace scored, followed by misses for Jamie Millar, Adrian Kiatkowski and Chris Rooke.
In sudden death the hosts kept their cool with Neil Forsyth, Shaun Bayes and then Buck taking them to victory.
Earlier, strikes from Joe Bayes and Wallace had put the hosts in front, but Newlands drew level with a goal either side of the interval.
Hird looked to have sealed the win for Commercial, who then had two goals disallowed before the visitors levelled with the last kick of the game.
With the hosts reduced to nine men for extra-time, as Louis Hird and Luke Chambers had to leave early due to work and they had used their sub earlier on, they hung on for penalties and finally overcame a plucky Newlands side.
Heslerton edged through 5-4 on penalties after having to work hard 3-3 at home to second division side Cayton Corinthians, who also played extra-time with only nine men.
A Danny Collins double in the opening 10 minutes got the visitors off to a flying start, but Dan Blanchard’s strike gave Heslerton hope.
A 25-yard free-kick from David Thompson made it 2-2 then a stunning 30-yard strike from Josh Beach put Heslerton in front before half-time.
Cayton refused to buckle and drew level early in the second half through a Corey Towell effort, but when player-boss Jonny Best was dismissed for a second caution midway through the second half the odds were against an away win.
Heslerton piled on the pressure but Cayton defended superbly, and due to injury they were reduced to nine men for extra-time but still held on for the penalty shoot-out.
Billy Bown scored from the spot for Heslerton, and although Gareth Driver hit the post, further successful spot-kicks from Beach, Mikey Webster, Mike Clark and Tony Cass secured the win for the hosts as Cayton missed two of their penalties.
Heslerton boss Dean Storry said: “I feel sorry for Cayton as they started really well and I couldn’t see us coming back but the lads fought back well and we deserved it in the end.
“The whole team deserves a share of the man of the match award as they dug deep throughout the 120 minutes.”
Cayton’s Damon Cook echoed Storry’s sentiments, saying: “I am so proud of the way that the lads played especially when reduced to 10 and then nine men.”
Trafalgar hit back from 1-0 down to claim a 7-2 win in the Scarborough FA Sunday Cup at Division One rivals West Pier.
Sam Garnett put Pier in front but a Neil Thomas free-kick levelled the scores and central midfielder Gary Thomas made it 2-1 before half-time.
Neil and Gary Thomas scored a goal apiece to give Traf some breathing space in the second half, and sub Alex Sheader and Kurtis Henderson then struck to make it 6-2.
Martin Cooper pulled a goal back for the hosts but Chris Dove rounded off the scoring for the away team.
Neil Thomas was named as the Traf man of the match for a fine game up front.
Adam Entwhistle scored four as Division One side Whitby Wanderers had to work hard for a 6-3 home win against Barrowcliiff Reserves.
A James Landers free-kick and a strike from Entwhistle put Wanderers 2-0 up, but James Galashan pulled a goal back for ‘Cliff.
Entwhistle then made it 3-1 but a well-worked move then saw Joe Sunter head in at the far post to keep the visitors in the tie.
Striker Entwhistle completed his hat-trick to make it 4-2 after the break and then Whitby’s man of the match Sam Cornforth added a fifth before Adam Martin rounded off another fine Barrowcliff move to give them hope.
Entwhistle then hit his fourth to secure the win for the hosts.
Right-back Ryan Goodworth and right-sided midfielder Aiden Cooper shared the man of the match award for the away side.
FILO remain in top spot in Division Two after a hard-earned 3-0 home win against previously unbeaten Ayton.
Lee Brennan opened the scoring for the hosts, the villagers could have levelled from the penalty spot, but Kieran Noble saved Tyson Stubbings’ spot-kick.
Brennan then doubled his side’s lead with a powerful left-foot strike after a free-flowing move.
Ayton stepped up a gear after the break but FILO defended well and hit the villagers on the break five minutes from time when Phil Raisbeck scored to seal the win.
Dan Brown was the man of the match for FILO.
Roscoes Bar continued their revival with a 7-0 home win against Alma.
Tom Allen opened the scoring after collecting a Mark Kenyon pass, and Allen then returned the favour by crossing for Kenyon to volley home from 10 yards.
After the interval, Allen scored two quick goals to complete his hat-trick, then Jamie Wray, making his debut, scored two cracking goals to wrap up the win.
Harry Harman, also on as a sub scored the seventh with a neat strike through the Alma keeper’s legs.
Gary Hepples and Allen both impressed for Roscoes Bar.
Curtis Rose smashed in four goals and Danny Glendinning three as Trafalgar Reserves powered to a 10-1 home win against Crown Tavern.
Luke Jones netted a brace for Mikey Barker’s side while a Martyn Ferrey free-kick rounded off the scoring for Traf, whose man of the match was striker Rose.