Boro reached the last eight of the Uefa Cup having progressed on the away goals rule against Roma on this day in 2006.
Boro took a 1-0 lead to Italy courtesy of a Yakubu penalty and they doubled their aggregate advantage when Jimmy Floyd Hasselbaink turned in Stewart Downing’s cross from the left just after the half hour.
Mark Schwarzer did well to keep Roma at bay, but they eventually pulled one back when Amantino Mancini clipped the ball beyond the Boro keeper to give the home side a lifeline before the interval.
Mancini despatched a penalty on 66 minutes after Stefano Okaka Chuka was brought down by Ray Parlour, however Roma still required another goal to go through.
But it was Steve McClaren’s Boro who prevailed despite losing 2-1 on the night to set up a quarter-final meeting with FC Basel, before going on to reach the final for the first time in our history.
Watch extended highlights above.