The former Leeds United, Newcastle United, Real Madrid and Tottenham Hotspur defender picked up his sole honour in the domestic game when he helped Spurs beat Chelsea to lift the competition formerly known as the Carling Cup in 2008 on a memorable early-spring occasion at Wembley.
Woodgate famously scored the winning goal in extra time in Spurs’ 2-1 victory over their big London rivals in front of a crowd of almost 88,000 and was also named as man-of-the-match following a typically exemplary performance.
Now leading his hometown club, Woodgate’s latest experience of a competition now known as the Carabao Cup will be played out in front of substantially lower crowd at the Riverside Stadium, but the occasion will still carry significance for the Teessider.
Woodgate has made great play of the fact that young players will be afforded opportunities under him and a number of academy talents are likely to be blooded tonight in a tie which pits two clubs together whose youth policies have earned much praise over a number of years.
Alongside the fresh-faced talent on show for Boro, the likes of George Saville, Marcus Tavernier and recent signings Marc Bola and Marcus Browne are likely to be handed a chance to impress.
Last six games: Middlesbrough WLWWDL; Crewe WWWLLW.
Referee: M Salisbury (Lancashire).
Last time: Middlesbrough 1 Crewe 0, February 25, 1998; Division One.