Middlesex 376 (Simpson 92, Holden 86, Stoneman 67, Hollman 52, Pattinson 4-65) and 63 for 0 trail Nottinghamshire 551 for 8 dec (James 155, Mullaney 79, Patterson-White 50, Hollman 4-122) by 112 runs
Middlesex face a battle to save a draw after Division Two leaders Nottinghamshire continued to hold the upper hand in their top-of-the-table clash in the LV= Insurance County Championship.
Despite an impressive fightback from 106 for five, Middlesex were forced to follow on 175 runs behind after Nottinghamshire had dismissed them for 376.
Openers Mark Stoneman and Sam Robson survived 20 overs to take Middlesex to 63 without loss at the close. They could be in for a tough final day with Nottinghamshire still 112 in front, although a benign pitch may make their task easier.
James Pattinson finished with four for 65 and Dane Paterson three for 97 after John Simpson (92), Max Holden (86) and Luke Hollman (52) had mounted a gritty effort to keep their side in the game in response to Nottinghamshire's 551 for eight declared.
Middlesex had begun the day needing to regroup after losing Stoneman shortly before Monday's close, a dismissal that felt like a critical breakthrough by left-arm spinner Liam Patterson-White, and Nottinghamshire had their tails up when Pattinson removed nightwatchman Tom Helm with his first ball of the morning, leaving them five down and 445 runs in arrears.
But on a hard, dry surface that was still playing true for the batters, their second attempt at regrouping succeeded, with Simpson and Holden able to make steady progress. Patterson-White set himself for a long day, unable to contain a yelp of exasperation from time to time when the ball spun past the bat without material gain, while none of the seamers was able to create any real drama, even when Pattinson started bowling short at Holden to a 6-3 leg side field in the half-hour before lunch.
Both parties in the partnership went past fifty, in Holden's case for the fifth time this season, and had added 111 out of 217 for five at lunch, which left them still 334 behind but in better shape than they might have feared.
The afternoon brought more of the same, yet it ended with Nottinghamshire in the ascendancy after both fell without reaching three figures.
Holden went just before the second new ball became available, caught at slip off Ben Slater, who has kept his offspin mothballed for most of his career but has employed it twice to good effect this season in similar circumstances and now has two first-class wickets to his name.
Alex Thomson of Derbyshire was his first victim. Whether Holden was genuinely was a moot point, certainly in the opinion of Holden himself, who appeared to have avoided any contact with a ball that spat up and over his head, dropping to his haunches in apparent disbelief as umpire Paul Baldwin raised the finger.
Whatever the merits of the decision, it ended a partnership of 142 for the sixth wicket. Simpson, though, certainly did get a touch as he perished eight short of what would have been his second hundred of the season, driving at a ball from Pattinson but succeeding only in edging into the hands of Joe Clarke at slip.
He and Hollman had added 73 for the seventh wicket, the 21-year-old leg-spinning all-rounder completing his half-century soon after tea with his 11th boundary.
Martin Andersson's positive approach helped Middlesex to a fourth batting bonus point and raised the possibility that the follow-on might be avoided.
But those hopes receded as Hollman hooked Paterson into the hands of deep square leg, the South African picking up a third victim when Toby Roland-Jones was lbw trying to work the ball to leg. Pattinson wrapped things up when Andersson miscued to midwicket.
