The Sky Blues secured their fourth victory of the season after winning 2-0 at the Coventry Building Society Arena this afternoon.
The two sides exchanged chances in the first half, with neither able to open the scoring.
Second-half goals from strike pair Viktor Gyökeres and Martyn Waghorn secured all three points for City.
Martyn Waghorn came close in the opening stages, with an acrobatic attempt, but fired narrowly over from Jamie Allen’s cross.
The visitors responded swiftly through Marcus Tavernier, who whipped a dangerous ball across the face of goal, before testing City keeper Simon Moore with a long-range strike moments later.
Waghorn continued to trouble the visitors and nearly found the back of the net after poking the ball past Sol Bamba and firing low to force Joe Lumley into a save at his near post.
City came close again, following a intricate passage of play between Callum O’Hare and Waghorn in the box, but after a goal-mouth scramble, the Sky Blues were unable to convert the chance.
HALF-TIME: Sky Blues 0-0 Middlesbrough
Middlesborough started the second half on top, coming forward through Uche Ikpeazu, but a spectacular triple save from Moore in the Sky Blues net kept the game level.
After Boro’s close call, City continued to mount their attack in search of a goal and came inches away when Gustavo Hamer’s cross nearly sailed in directly from a corner.
Following a spell of pressure from City, Allen latched onto a loose ball and picked out the run of Gyökeres charging down on goal, leaving the Swede to round Lumley and slot the ball away to give City the lead.
The visitors searched for an equaliser and nearly found one when Matt Crooks’ glancing header clipped the crossbar, going over for a goal-kick.
Martyn Waghorn doubled the lead and secured in stoppage time with a weak-foot finish, wrapping up the win for the Sky Blues.
FULL-TIME: Sky Blues 2-0 Middlesbrough
Scorers: Gyökeres (72’), Waghorn (90’)
Cards: Hamer (26’), Howson (32’), Tavernier (32’), Bamba (63’)
Attendance: 18,515 (2649 away)
Sky Blues Xl: Simon Moore (GK), Fankaty Dabo, Dom Hyam, Kyle McFadzean (C), Jake Clarke-Salter (Michael Rose 75’), Ian Maatsen (Todd Kane 83’) , Jamie Allen, Gustavo Hamer, Callum O'Hare, Martyn Waghorn (Matty Godden 90’), Viktor Gyökeres.
Unused Subs: Ben Wilson (GK), Ben Sheaf, Jodi Jones, Tyler Walker.
Middlesbrough XI: Joe Lumley (GK), Anfernee Dijksteel, Grant Hall, Dael Fry, Sol Bamba, Isaiah Jones (Duncan Watmore 75’), Marcus Tavernier, Jonny Howson (C), Matt Crooks, Uche Ikpeazu (James Lea Siliki 63’), Onel Hernandez (Andraz Sporar 63’)
Unused Subs: Luke Daniels (GK), Toyosi Olusanya, Lee Peltier.