Amid conditions which event organiser Richard Patton described as "the worst in living memory", 54 runners finished the world's oldest handicap fell race, which dates back to 1862.
Winskill finished the gruelling 3.25 mile course in a time of 21.51. South Yorkshire Orient runner Shane Lynch crossed the line first in 25.22.
The handicap format allowed a staggered start based on runners' best times – designed to ensure a close finish.
Involving 800ft of climb, the route started at Hallam Cricket Ground at 8pm before heading across the River Rivelin bridge, looping round Stannington Church and back up the gruelling Den Bank hill on return.
Pippa Wilkie, of Hallamshire Harriers, was first across the line in the women's race, but Fat Boys runner Judith Jepson gained the fastest actual course time of 27.08.
Patton thanked his wife Channah for co-organising the event which was sponsored by the Taylor and Emmet law firm. He said: "They supplied the prizes and the moral support."
Winskill won the Burbage Skyline fell race earlier this month, finishing ahead of Dark Peak club mates Neil Northrop and Rob Little.
The course record time for the Hallam Chase is held by former Hallamshire Harrier Trevor Wright, a silver medallist in the marathon at the 1971 European Championships.
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