Bolo Zenden played a pivotal role in securing our first major trophy, scoring the winning goal from the spot in the Carling Cup final victory against Bolton Wanderers.
Seen as the natural successor to Marc Overmars when he burst on to the scene at PSV Eindhoven, the former Barcelona man initially arrived at the Riverside on loan from Chelsea in the summer of 2003.
An ever-present in the side, the Dutchman quickly became a firm favourite among Boro fans when he slotted what proved to be the winning goal in Cardiff in the Carling Cup final, despite slipping as he struck the ball past Jussi Jaaskelainen to give us a two-goal lead.
Even though Kevin Davies pulled one back for Bolton to reduce the deficit, Boro would hold on to end a 128-year wait for our first major piece of silverware, with Zenden named man of the match.
After his loan spell drew to a close, Zenden penned a one-year permanent deal with the club.
Although he sustained a broken hand, he would miss just two of Boro's 51 games in the 2004/05 campaign, and bagged a brace in a memorable win over Lazio in the Uefa Cup on home soil.
Zenden would move on after his contract expired at Boro, and went on to join newly-crowned Champions League winners Liverpool, with further spells with Marseille and back in the North East with Sunderland following after he departed Anfield.