In a rain-swept match it was Boro who made the early running with Gareth Southgate and Carlos Marinelli going close, but Wednesday took the lead after 9 minutes through Jon Beswetherick.
It took Boro just over 10 minutes to equalise when Franck Queudrue headed home a Marinelli free-kick. Boro continued to create chances throughout the first half to failed to convert, so the match remained level until half-time.
The second half started quietly and it took over 15 minutes before there was a real chance, which fell to Noel Whelan, but his drive was deflected wide.
Robbie Stockdale almost gave the Owls a bizarre lead but his back header drifted over the corner of the bar, with Mark Schwarzer stranded.
Boro sealed a deserved victory with 4 minutes remaining when Maccarone connected with a deep cross from David Murphy to head past Kevin Pressman in the Sheffield goal.