Ramires and Victor Moses goals after the break sealed an Old Trafford tie following a lacklustre first half from the holders and Champions League winners on Teeside.
The smallest man on the pitch, Scott McDonald, was the first to cause any trouble as he glanced a header just wide, sneaking in to meet Nicky Bailey's curling ball from the right on 25 minutes.
Mustapha Carayol then glided in from the left to thump a shot at Petr Cech, who palmed away on the bounce before John Terry bundled clear.
The hosts failed to clear their lines and the loose ball fell to Ramires, who saw his shot deflected off Fernando Torres and past helpless Boro keeper Luke Steele.
Substitute Eden Hazard almost made it two with a quarter of the game to go as his curling shot beat both Steele and the far post.
Ishmael Miller thrashed a late snapshot narrowly over, but it was too late for the side who must return to fixing their shocking Championship form.
Chelsea: Cech 6, Ferreira 6, Ivanovic 6, Terry 7, Bertrand 6, Moses 7, Ramires 6, Oscar 6, Ake 7, Benayoun 5, Torres 5. Subs: Hazard (Benayoun 58) 7, Luiz (Moses 76) 5 Marin (Oscar 79) 5. Not used: Turnbull, Cole, Lampard, Ba.
Middlesbrough: Steele 6, Bailey 6, McManus 6, Bikey 6, Friend 6, Carayol 6, Leadbitter 6, Williams 7, Haroun 6, Main 6, McDonald 6. Subs: Hines (Bikey 36) 5, Miller (Main 62) 5, Zemmama (Carayol 73) 5. Not used: Leutwiler, Emnes, Ledesma, Smallwood.
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