12 months ago the two teams met at the same stage of the competition, with Richards on loan at Fiorentina from Manchester City.
He was selected to start the match against Tottenham, and played a starring role in helping the Serie A side win in Florence, securing a 2-0 victory to take the tie 3-1 on aggregate.
Richards was impressive that night, winning duels and playing with confidence - a far cry from the last time he was seen on a football pitch.
In the summer he signed with Aston Villa, convinced to make the move by former Spurs boss Tim Sherwood, and neither could have imagined the unmitigated disaster which would follow.
Sherwood was fired by October after winning just one league game, and in the months since under Remi Garde, they have managed only two victories, and look destined to suffer relegation to the Championship, currently eight points from safety.
At the weekend Villa suffered one of their poorest results in recent memory, losing 6-0 at home to Liverpool. The team looked lifeless and bereft of confidence.
It was the exact opposite of Richards' energetic display in Florence against Spurs last year, and he may well be reflecting this evening, trying to work out where it all went wrong.