Simms had a couple of chances to make it three, but Boro halved the deficit when Whittaker volleyed into the bottom corner from Alfie Jones’ flick-on as they kept a corner alive.
Coventry’s number nine was denied shortly after half-time by Brynn, but one thing the Teesside club have shown all season is spirit and it was in evidence here for new Swedish boss Hellberg.
They started the season impressively under Rob Edwards, until he departed for Wolverhampton Wanderers earlier this month, but Hellberg will inherit a team still well-placed.
Whittaker, a player reinvigorated from his early struggles at the club, had a piledriver brilliantly tipped over by Carl Rushworth, but his side were level from the following corner as Thomas inadvertently turned it into his own net.
Scotland forward Conway should have completed the turnaround, only to put the ball over from six yards after Callum Brittain’s cross had opened up the defence.
They paid a heavy price as Kitching restored the lead, with an instinctive first-time finish after Brynn had denied Thomas from making amends for his own goal.
And before Boro could regroup, Simms headed in at the end of another slick attack to demonstrate what a tough job the rest of the Championship will have in reining in Lampard’s leaders.
