The goalkeeper had repelled everything the Barclays Premier League side could throw at him when, 23 minutes into extra time, in his desperation to claim Mido's deflected shot, he helped the ball into his own net to hand Boro a quarter-final clash with Cardiff.
It was the most unkind of misfortunes for the 29-year-old, who had turned in a superb display to keep out the Teessiders' record signing Afonso Alves - on two occasions - Luke Young, Stewart Downing and Tuncay Sanli.
Indeed, had James Beattie's 90th-minute shot crept inside Mark Schwarzer's left post rather than gone marginally outside it, it would be the Blades welcoming Cardiff to Bramall Lane in the last eight.
On the balance of play, Boro were good value for their victory, but having dominated for long periods, they had failed to make the most of their pressure until they were handed a large slice of good fortune in front of a crowd of 28,108.
With Gareth Southgate's side needing replays in each round of last season's competition before going out in the quarter-finals at the second attempt at Manchester, and the Blades having drawn their last six matches, the chances of the tie ending after 90 minutes always looked remote.
However, had Alves had his way, Boro could have been all but home and dry by the time the whistle brought an end to the first half.
The Brazilian could barely believe his luck when nine minutes into his full debut, he ran unmarked onto Fabio Rochemback's corner in front of goal.
A square connection would have seen the ball fly into the net with Kenny stranded, but his glancing touch simply sent it wide of the far post and let the visitors off the hook.
But a man who scored 49 goals in as many games for previous club Heerenveen was never likely to dwell on that miss or to have to wait long for another opportunity, and his chance duly arrived 10 minutes before the break.
Matthew Kilgallon was booked for his trip on Alves 30 yards out, but it was Kenny who had to pick up the pieces and the South American blasted in a dipping, swerving free-kick which the keeper did well to parry.
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