Ten-man Scarborough Athletic battled whole-heartedly in the final of the North Riding FA Senior Cup on Wednesday night, but Middlesbrough's youngsters edged the final at the Riverside by a single goal.
Steve Kittrick's men controlled much of the game, but a missed penalty and a sending off cost them in the end.
Boro's two-week rustiness was evident in the opening minutes of the game, as the youthful Middlesbrough side rolled the ball around the park in composed fashion.
But Boro began to show their worth after this, with Max Wright coming to the fore on the right side.
It was the Grimsby loanee, in his last game for the club, who created the perfect opportunity for Boro to take the lead on 10 minutes.
Wright burst into the box, but his progress was ended by a crude challenge from Patrick Reading.
James Walshaw stepped up, but his low spot-kick was met by the firm hand of Brad James, who pushed the ball away to safety.
Middlesbrough began to eek their way back into things, forcing a few saves out of Boro keeper Tommy Taylor.
The best of these saw Taylor flinging himself to the right to tip Mitchell Curry's shot out of the bottom corner.
Boro were still the biggest threat at the other end, with Wright again giving Reading a roasting before drilling at goal. James got down to block and Walshaw was crowded out as he tried to gobble up the pieces.
Middlesbrough had one last opportunity before the interval, with striker Luke Armstrong wriggling in on the Boro goal. Taylor was quick from his line though and he made himself big to block the effort.
After more probing from both sides when the second half got underway, Boro were dealt a hefty blow 10 minutes after the resumption.
Striker Armstrong again managed to get himself free and Boro defender Sam Hewitt pulled him back when through on goal. It seemed as though Hewitt's partner Josh Snowden would sweep around, but referee Chris Keightley thought otherwise, giving the Boro man a straight red card.
Further salt was rubbed into the wounds soon after when Hayden Coulson rolled the ball into Mitchell Curry on the edge of the box, he spun and fed a shot into the bottom corner.
The whole picture of the game had been changed, with Boro being forced to retreat and Middlesbrough going in for the kill.
Taylor further earned his corn with a couple of good stops and when he was beaten from close range by Armstrong, he was saved by the linesman's flag.
Boro tried to come again, going in search of their second piece of silverware of a fine season.
They found it a challenge to break down a sharp and organised Middlesbrough back-line though.
When they did, with just a few seconds remaining of normal time, Walshaw crashed the ball into the sidenetting after some neat footwork from sub Jorom Slew.
The Championship team's youngsters saw out the final moments to steal the glory and the trophy.