Angel showed their nerve from the penalty spot to dump rivals Trafalgar out of the North Riding Sunday Cup.
Joel Ramm's Trafalgar side faced an uphill battle from the 10th minute when Jamie Patterson was sent off for foul and abusive language.
Angel took the lead on 20 minutes when Matthew Griffiths headed in from a Jackson Jowett corner.
To their credit though, the 10 men of Traf dug deep and battled hard and were rewarded with an equaliser 10 minutes later when Jack Ramos stooped to re-direct Danny Glendinning's shot past Angel custodian Joe Wright.
Traf's stand-in keeper Nathan Vernon made a couple of good saves in the second half, but chances were at a premium for both sides and the game finished 1-1 and went straight to penalties.
Martin Cooper, Cameron Dobson, Neil Thomas and Kurtis Henderson all scored from the spot to seal Angel's 4-1 win in the shoot-out, Luke Jones seeing his effort saved by Wright and Glendinning dragging his effort wide after Danny Price had scored for Traf.
Angel boss Dan Jones was delighted to progress, despite not being overly impressed with his side's performance.
"We're really pleased to go through, despite us not being anywhere near our best," said Jones.
"It was good to get the monkey off our backs a bit after losing to them in the final last year.
"We're still on to win all five competitions we're in, so there's still a lot to play for."
Jones singled out centre-backs Gary Thomas and Kurtis Henderson as his side's star men.
Traf boss Ramm was delighted with the efforts of his side, especially after going down to 10 men so early in the contest.
Ramm said: "I want to praise every single one of the players who turned up and battled for so long with 10 men.
"I thought we just about shaded it, despite being down to 10 men for so long."
Angel are now through to the semi-finals of the competition.
Newlands edged out Valley 2-0 in the Senior Cup.
Jack Hakings opened the scoring for Lee Dolan's side with a neat finish from 18 yards.
Kile Fields sealed Newlands' passage to the semi-finals with a stunning strike from long-range.
Kyle O'Toole was Newlands' star man, with right-back Ben Dolan also impressing.
Boss Dolan said: "It's an outstanding effort from the lads to get through to another semi-final."
Despite their defeat, Danny Appleby impressed in the Valley midfield, with James Barber and Jake Adams also solid in their defence.
Cask cruised into the next round with a 4-0 win at Fylingdales.
Callum Myers smashed in a hat-trick to guide Dan Sheader's side to victory, one of his goals a superb free-kick from long-range.
Zac Hansen hit Cask's other goal in their victory.
Boss Sheader singled out his side's defence and keeper James Burrows, who made an outstanding save in the first half.
Roscoes Bar beat Castle Tavern 5-2 in the Goal Sports Trophy.
Matty Rowley hit two for the victors, with their other goals coming from Gary Hepples, Mark Kenyon and Tom Allen.
Sean Rowley was singled out as Roscoes' man of the match by boss Lee Paterson.
Paul Mills and Shane Holt found the back of the net for Wayne Shaw's Tavern side.
Goalscorers Holt and Mills were Tavern's stand-out performers.
Cayton's clash against Saints was off due to a waterlogged pitch.
DON'T MISS!! 17 OF OUR OLD SUNDAY LEAGUE TEAM PICS / http://https://www.thescarboroughnews.co.uk/sport/football/photo-focus-17-sunday-league-team-pictures-1-9581395
NRCFA SUNDAY CHALLENGE CUP
Angel 1-1 Trafalgar (Angel won 4-1 on pens)
Fylingdales 0-4 Cask, Valley FC 0-2 Newlands
GOAL SPORTS TROPHY
Cayton P-P Saints, Roscoes Bar 5-2 Castle Tavern