Adam Forshaw headed a judging panel for local school children competing in the Premier League Enterprise Challenge at the Riverside Stadium.
The Enterprise programme, here co-ordinated by Boro's official charity MFC Foundation, began in 2009 and is run in partnership with Sport Relief.
It has seen over 11,000 13- to 15-year-olds take part in educational sessions, using the business model of professional football clubs to engage young people.
Local schools Acklam Grange, The King's Academy, Unity City Academy, Egglescliffe School and Beverley School For Autism all entered teams into this year's national competition, with the brief focusing on fan engagement in the USA.
A panel consisting of MFC Foundation Chief Executive Karen Wilkinson-Bell and MFC Foundation Trustee John Baker as well as Forshaw awarded the victory to The King's Academy, whose innovative idea was to link up with an NFL team as a way of forming links with American fans.
Adam Forshaw commended all of the teams' efforts, as he handed out autographs and posed for photographs with the young people.
"It's a daunting task for the kids to come and give their pitch," he said.
"I wouldn't like to do something like that so they all did really well, and it was a tough decision in the end."
"I think they [The King's Academy] were very thorough. It was a joint decision and I think they came really well prepared."
Beverley School For Autism were one of the team's competing in the event on Wednesday, a specialist school which cares for and creates a peaceful environment for young people with autism.
Tyler Binks, 15, spoke about the challenge of presenting in front of a big crowd.
"I felt a bit nervous at first, but once I got up in front of everyone it wasn't so bad. I've done a couple of presentations before with my associates at school, and at first we were all very nervous but we were quite happy with our efforts.
"I just tried my best, and that's all I could do."
Forshaw was particularly impressed by the Beverley team, as he said: "Their group obviously has a little bit of difficulty getting up and talking in front of people, so for them to just get to the stadium and have an experience like this is a great education for them."
"It's a credit to them."
Fresh from the win over Hull City earlier in the week, Forshaw was happy to show his support for MFC Foundation.
"It takes you away from football; today was my day off but I think it's something different to do and I enjoyed doing it last year," he said.
"When they asked be back I was happy to, it's been a good day."
MFC Foundation's Education Coordinator Ruth Watson said of the event: "We've been really lucky today to have 40 young people from the area competing. They've been working so hard on it for weeks now and it came through in the standards of their presentations.
"We're very proud of them as always, and we're very happy to have The King's Academy going forward to hopefully getting us through to the national finals."
Having won the competition in 2012, Middlesbrough will now move on to the regional heats of the event, which is held at Stoke City.