The Blues won the trophy when the two faced each other in the 1997 final when Roberto Di Matteo scored a 30-yard screamer after just 42 seconds of play.
Since then, the fortunes of both clubs have changed dramatically with Chelsea tasting reaching the giddy heights of European glory whilst Middlesbrough have been absent from English football's top table since 2009.
The Blues failed to draw a save of any real note from Jason Steele in the first-half in what was a hotly contested 45 minutes of counter-attacking football. Boro had the best chance as Petr Cech was caught out by an awkward bounce, only for John Terry to appear to clear the danger.
The last thing Chelsea need is a replay as they have played twice a week, every week for three months, excepting the international break in January.
Whatever Rafa Benitez said at halftime worked, as a failed attempt at a volley from Yossi Benayoun fell kindly back to him, and he was able to lay it off to Ramires, who produced a strike of Brazilian quality to make it 1-0. The Israeli then made way for Eden Hazard, who played a lovely on-two with Oscar before squaring it to Victor Moses for a close range tap-in.
Middlesbrough rallied late on in the game, but a fine Petr Cech save from a Merouane Zemmama free-kick meant that the FA Cup holders progress to face Manchester United at Old Trafford in the quarterfinals.
Every player starts on 5/10 and points are awarded or deducted based on attitude, work-rate and contribution to the game. A goal scored by a defender is weighted higher than one scored by a striker and red cards and missed penalties get an automatic 1.0 deduction. Experience and form are taken into account.