FOUR of the seven second-round games in the newitts.com Beckett League's Marisa Trophy had to be decided by penalty shoot-outs.
Heslerton came a cropper after dominating against Kirkdale United from start to finish.
Heslerton had 15 efforts at goal with 10 on target but they could not find the back of the net as the game ended goalless. Goalkeeper Darren O’Grady was United's man of the match, though Heslerton number one Mick Norman also had to make two superb saves midway through the second half.
Kirkdale won 3-0 on penalties - Phil Ward, Tony Dodds and Alex Croall the marksmen.
It was Kirkdale's second shoot-out victory of the week, having done likewise at Thornton-le-Dale reserves last Wednesday night in the second round of the Panasonic League Division 2 Cup.
Lee Timms was Heslerton's man of the match.
Union Rovers 2nds fell to Easingwold Town 3rds on penalties, after fighting back with 10 men in normal time.
A Gary Raper penalty had put Easingwold ahead in the first half, with Union’s Ashley Cooke sent off for hand ball on the goal-line.
Union equalised after 70 minutes through Richard Abbey.
Easingwold won the shoot-out 4-2 thanks to successful penalties by Gary Raper, Richard Brian, Tony Raper and Brendan Carrick. Abbey and Chris Armstromg missed for Union, as did John Dey for the visitors.
Midfielders Ryan Cooper (Union) and Sean Dixon (Easingwold) were the men of the match.
A thrilling Pickering derby saw Ryedale Sports Club reserves edge Pickering Knights 7-6 on penalties after the tie had ended 3-3.
Ryedale were two up inside 10 minutes as Tim Whincup scored after taking advantage of a long throw by Alex Ibbotson, and John Ellis headed in another Ibbotson long throw.
Knights hit back after 40 minutes through Graham Atkinson, but within a minute Ryedale regained their two-goal advantage through Tim Whincup after yet another long throw by Ibbotson was chested down by Matty Gardner.
Atkinson again brought the Knights back into the game after 50 minutes and, 10 minutes from time, James Boak equalised with a superb header.
Boak turned from hero to villain, though, in the shoot-out. Ryedale's goalkeeper, Dave Whitelock, was conversely the star, saving from Miles Dale and, in sudden death, from Boak.
Successful for the Knights were Atkinson, man-of-the-match Greg Fawcett, Steve Temple, Josh Brittain, Rowan South and Josh Fawcett.
Harry Reed missed for Ryedale, but man-of-the-match James Reed, Ryan Boyes, Gardner, Ellis, Whincup and Nen Thompson netted before Matty Bell sent them into the quarter-finals.
Duncombe went two up in the first half through Ben Richmond and Cory Taylor, but Dec Copland headed Settrington back into the game after the break and Park then lost play-maker David Elkington to injury.
Settrington, for whom Rory Darley starred, equalised on the hour with a rare George Mattinson goal - a wind-assisted cross-cum-shot from 35 yards.
Copland and Mattinson also found the net during the shoot-out, with Gareth Thistleton and Nick Bell likewise successful for Setty.
The impressive Cory Taylor and Jack Wright scored from the spot for Duncombe Park.
Gillamoor won 3-2 at Rosedale in an all first division clash.
Gillamoor shot into a three-goal lead, captain Andrew Claughton's two strikes sandwiching a special goal by man-of-the-match left-midfielder Nathan Blacklock.
Rosedale, for whom Matthew Tyreman was man of the match, came back with two goals in the last 10 minutes - a Martin Myers penalty and a last-minute Stewart Dowson effort.
Slingsby edged Snainton reserves 2-1 in an all-division two clash.
An own goal and a Sean Keefe strike put them two up by half-time. Snainton did much better in the second half and Josh Hill halved the deficit but they couldn’t find an equaliser.
Sam Collings (Snainton) and Brent Wilson (Slingsby) were the men of the match.
Heslerton won 3-1 at Thornton-le-Dale reserves.
A Robbie Preston brace - a header and a well-struck shot - was supplemented by a first goal for the club by 16-year-old Josh Hunter, the man of the match. Darren Davies replied late on for Thornton, for whom centre-back Olly Baxter impressed.