Vance Breeze and Michael Ross rode the Harleys in the 1982 Classic race; Ross retired on the first lap.
The other rider to ride a Milwaukee heavyweight was Dave Hughes in the 1975 Classic. I have a wonderful shot of him in level flight over Ballaugh, bet it made the ground shake on landing!
Dave retired on the last lap; his best time was 23.14.8. I gather it was not his favourite mount round the Island! I think the machine was entered by Pratt's of Greenwich. Saw the ex-Hailwood Benelli single for sale in that shop also.

I wonder if this could have been the identical machine ridden by Hailwood's 'team mate' for the 1962 TT,Alan Dugdale?