Tonight Boro set out on a journey they hope will enhance the club's reputation in a tournament they have previously won.
Rotherham United are the visitors at Bishop Auckland's Heritage Park, with a 7pm kick-off.
"It is as important as the FA Cup at our level," says Academy Interim Head Coach Craig Liddle. "The lads were excited when the draw was due to be made. Everyone who has ever been involved, including myself, can remember their experiences."
In charge of the team tonight will be Mark Tinkler, he too has very fond memories of the competition.
It was with Leeds United that the Bishop Auckland man first came to prominence, working his way through the junior side at Elland Road where the highlight was winning the FA Youth Cup against Manchester United.
"Yes, those games against Manchester United in the final of the FA Youth Cup were special," he says with a smile.
"We were up against the United side that had David Beckham, Paul Scholes, Ryan Giggs, that era.
"Those are memories I have never forgotten, now we're challenging today's players to go and make their own. They have a great opportunity."
Boro are a Category 1 Academy, Rotherham are Category 3 and the two sides met in a pre-season friendly where Boro ran out 4-1 winners. All factors you would think would swing the tie in Boro's favour.
But Interim Head Coach Liddle acknowledges: "We know it won't be easy. With due respect this is their (Rotherham's) cup final and they're going all out to cause an upset.
"We're without our goal man, Mitchell Curry, he will be out for 10-12 weeks after dislocating his shoulder. He'll be a big loss, but it will give somebody the chance to step up and impress."
Academy football is predominantly about development, but Liddle admits the focus is slightly different in this game.
"This competition is about results. Our league programme is about development and we're very mindful of what can happen in these games. Everyone is looking forward to it."