Newlands Reserves striker Zak Hansen struck a magnificent seven goals as the 10-man second division side came back from 4-1 down to win 8-6 after extra-time against top-flight FILO.
The visitors made a flying start thanks to a Mark Swales hat-trick after Dave Welham's opening 35-yard strike which stand-in keeper Aiden McCallion failed to hold onto.
Shem Atkinson pulled a goal back from the spot for Newlands, who started the game with only 10 men, as the half-time score remained at 4-1.
Hansen then took centre stage smashing in three goals, the final one coming with the final kick of the 90 minutes to set up extra-time. This was an amazing achievement as Eric Hall was sent off in the early moments of the second half to reduce the hosts to nine men.
Hansen then hit three more as Newlands moved 7-4 ahead in the first period of extra-time, and although Phil Spencer and Simon Taylor struck to pull it back to 7-6, Hansen's seventh wrapped up the win.
Player-boss Dan Sheader said: "That is probably the best performance I have ever been part of the lads were all amazing although Zak definitely deserves the man of the match award for his seven goals.
"To beat a first division team with only10 men and then nine from early in the second half onwards is an amazing achievement."
FILO boss Les Brown said: "I am totally embarrassed by that result, the lads should have done a lot better."
Newlands' first team also moved into the next round with a 4-2 win at first division title rivals West Pier.
A towering header from Sam Hyde put Pier in front on the half hour mark, but Dan Freer levelled less than a minute later after fine work from striker Drew McCoubrey.
Newlands went in front from the penalty spot on the hour mark, McCoubrey slotting home after a penalty for handball by Sam Garnett, which was strongly disputed by Pier.
Martin Cappleman then pulled off a superb save to deny Pier a leveller and and 18-yard strike from Ben Luntley and a clever finish from Danny Glendinning wrapped up the win, although Rich Tolliday's cracking strike did pull it back to 4-2.
Hyde was named as the Pier star man for a superb central defensive performance, while McCoubrey was man of the match for Newlands.
Roscoes Bar also moved into the hat for the next round thanks to a 3-0 home win against second division Scalby.
Jamie Wray, Jack Brown and Matty Rowley scored the goals for the hosts.
A quick free-kick from Gary Hepples set up Wray to be one on one with the Scalby keeper and he headed into the bottom corner and shortly after Wray broke down the left beat a man and his shot was parried to Brown to tap into an open goal.
At the start of second half a short corner was played to the edge of the area for Matty Rowley to bend a shot into bottom corner.
Matty Rowley and Brown stood out in centre midfield for Bar, while Ben Dolan was man of the match for Scalby.
Harry Holden and Harry Sleep continued their fine form with two goals apiece as Cayton won 5-2 at a youthful Heslerton.
The home side took the lead through teenager Keaton Watson's fine finish but Jake McAleese's free-kick levelled the scores before Holden put Cayton in front.
Sleep then showed great skills to smash home a first-time shot from 40 yards back over the Heslerton keeper's head after he had miskicked his clearance.
Holden then struck again to make it 4-1, latching onto a superb through-ball by James Barber.
Sleep made it 5-1 after the interval, with the hosts improving after the break and Watson scoring a second in the 75th minute.
New recruit Watson was man of the match for Billy Bown's team, with Danny Alexander also impressing on the right wing, while McAleese was man of the match for Cayton, starting at left wing and dropping back to left-back.
Angel Athletic won 7-3 at home to Fylingdales Reserves in the second division, Ali Caw scoring a superb five goals for the hosts.
The leaders went behind early despite Fylingdales starting with only eight men due to a car breaking down, Dan Richardson putting the villagers in front.
The away side then got nine players on the pitch and Ali Caw levelled for Athletic, but Jake Faichney restored Fylingdales' lead with a 30-yard strike then two more players arrived to give them 11 players.
Caw smacked in another four goals to make it 5-2 at the interval, Fylingdales had a penalty saved early in the second half by Athletic's Scott Wardman.
Sub Neil Thomas smacked a shot into the top corner to make it 6-2, Adam Entwhistle pulled back another goal for the visitors after Andrew Marshall hit the bar from a free-kick, then debutant Macca Youngson, also on as a sub, scored to wrap up the win.
Caw was man of the match for Angel with Wardman pushing him close while Taylor Humble was the star man for Fylingdales.
Ayton Reserves suffered a 2-1 defeat at Crown Tavern,
Kyle Ireland put Tavern 1-0 up but Ayton equalised after half-time as Si Coupland scored after a fine pass from Luke Dunn..
Top scorer David Barber came back on up front with 15 minutes to go and got the winner with about eight minutes left to give new boss James Prethero a win in his first match in charge.
Right back Jake Stone was man of the match for the winners, while centre-back Dave Gaddass shone for Ayton while Richard Howes and Dunn also worked well in central midfield, striker Liam Bowman missing two good chances for the villagers, who put in a good display without any reward.