Liam Trevaskis's unbeaten 80-run knock propelled Durham to 350 runs as the Scott Borthwick-led side bundled out after adding just 94 runs to the overnight score.
Resuming 2nd day after hours of rain delay, Durham saw an awful start as their main man Ned Eckersley departed for the score of 58 off 133 balls as he could manage to add just one run to his overnight score. Ben Raine was next to follow as he was trapped on mid-on for a duck, leaving the visitors languishing at 267 for 7.
Trevaskis and Brydon Carse then made an imperative alliance of 58 runs for the 8th wicket to help Durham cross the 300-run mark.
However, Martin Andersson had other plans as he dismissed Carse for the score of 28 before Roland-Jones cleaned up the remaining two batters for five runs each. Liam Trevaskis remained unbeaten for the score of 80 off 156 balls.
T Roland-Jones was the pick of the bowlers for the home side as he finished the inning with four wickets to his credit, followed by Tim Murtagh, who bagged three wickets. Luke Hollman completed the inning with two, while M Andersson had one wicket in his kitty.
On the other hand, Middlesex buried the demons of their previous games and started their inning in an excellent way. Sam Robson and Mark Stoneman took the Durham bowlers to the cleaners as they shared an 86-run partnership before the recently appointed English Test captain Ben Stokes dismissed Mark Stoneman on 41.
Ethan Bamber was the next to follow Stoneman as Rushworth bowled a sharp length delivery to send the night watchman back for a duck, leaving the home side reeling at 88 for the loss of 2 wickets before the bad light stopped the game.
Durham 1st Inning: 350/10
Liam Trevaskis (80* off 156), Ned Eckersley (58 of 133);
Roland Jones: 4-72, Tim Murtagh: 3/43
Middlesex 1st Inning: 88/2
Mark Stoneman (41 off 69), (Sam Robson 41* off 68);
Ben Stokes: 1-8
Middlesex trail by 262 runs