Middlesbrough U21

The one trophy that matters in Middlesbrough's history arrived in 2003–04, when the first team won the EFL Cup.

Lee Cattermole was made club captain at 18 after coming through the academy, and later played for Wigan Athletic and Sunderland. Ben Gibson joined the academy at 12 and made more than 180 first-team appearances, captaining the side and helping Middlesbrough back into the Premier League before a move to Burnley. Dael Fry followed a similar path and has since captained the club himself past 240 appearances. Marcus Tavernier joined the academy at 14; he left for Bournemouth in one of the most expensive sales in the club's history, at £10.6m. Not every name linked to the academy actually belongs to it: Jonathan Woodgate left for Leeds United at 16 and only returned as an established professional, and Darren Fletcher's football education came at Manchester United, not Middlesbrough.