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Kent were indebted to the part-time bowling of Daniel Bell-Drummond for pegging back Middlesex's progress with the bat on day two of their County Championship clash at Canterbury.
The hosts lost early wickets and eventually trailed Middlesex by nine runs on first innings before the visitors reached 298-6 at the close.
Kent’s Jack Leaning, who was presented with his county cap at lunch on day two, said: “It didn’t quite go as we would have hoped this morning. We obviously lost a few wickets quickly and they bowled nicely and then batted nicely.
"We didn’t quite hit our straps with the ball. We’re a little bit frustrated as a group but sometimes that can happen and credit to Mark Stoneman.
"Hopefully we can make use of those conditions in the morning and there’s no reason why we can’t go out and chase.”
Kent began day two on 82-4, trailing by 65, and Ollie Robinson added just three to his overnight score when Ethan Bamber bowled him for 14.
Night-watchman Matt Milnes had reached 16 before pulling Martin Andersson to Luke Hollman, who took a tumbling catch at square leg.
Darren Stevens hit a single boundary before he was bowled by Bamber for four and Toby Roland-Jones sent Marcus O’Riordan’s leg stump flying for a 15-ball duck.
Grant Stewart was lbw to the next delivery, but Roland-Jones was made to wait for the hat-trick ball because Tawanda Muyeye (30) was out in the next over, caught behind off Andersson trying to flick the ball down the leg side.
A century from Mark Stoneman then put Middlesex in a dominant position. Stoneman hit 109 from 148 balls, with 16 fours.
Middlesex reached 32-0 at lunch, and although they lost Sam Robson for 19 when he edged Stevens to Robinson, Stoneman and Stevie Eskinazi put on 68 for the next wicket before the latter was lbw to Bell-Drummond for 31.
Stevens only bowled five overs and was forced off through injury as Stoneman and Robbie White reached 185-2 at tea.
Kent struck early in the evening session when Milnes got White for 38, the ball looping off his bat to Jordan Cox at first slip.
Stoneman eased his way to three figures with a glanced four to third man, but Middlesex suffered a middle order wobble when Max Holden left a ball from Milnes that bowled him for eight and Stoneman fell when he played on to Bell-Drummond.
Bell-Drummond (3-37) had Andersson caught behind for 15 but John Simpson (21 not out) and Hollman took the lead past 300, the latter smashing O’Riordan for six over cow corner on his way to 29 not out.