The lads did everything but score as they dominated the first hour in the quarter-final tie at the Riverside Stadium only to lose 1-0 when James Morrison's shot took a huge deflection and left keeper Paul Rutherford stranded.
Such was Spurs' dominance that Morrison's effort was only the home side's second effort at goal in the first 70 minutes and to rub salt into the wounds, David Tyrie's last-minute 'goal' was ruled out for a handball spotted by the linesman.
"We're a little disappointed," admitted coach Pat afterwards. "To lose, obviously, but I think it was a game that was there to win and I don't think we grasped the nettle enough on the night.
"We needed to be positive in certain areas and push players forward and that's something they should be able to sense themselves out there now.
"We created chances but it wasn't as fluent as Portsmouth earlier in the competition and in fairness Middesbrough tried to play.
"Having said that their keeper is a big, strong lad and we perhaps didn't have the rub of the green in the area but I just felt it was an opportunity missed.
"You could see the lads' heads go down after the goal but we hung in there and David then got the volley at the end that he insists wasn't handball.
"They lads will learn from it. Some of these lads will go further, some won't but they all have to deal with these things.
"But it would have been lovely to go to the semi-finals and I believe we've missed a golden opportunity, I really do."
Pat Holland believes Thursday night's sad FA Youth Cup exit at Middlesbrough was an opportunity missed by our Academy Under-18 side.