Democrat Andy Beshear claimed victory in Kentucky's governor vote, after a tight race in the conservative-leaning state.
Meanwhile, Democrats seized full control of the legislature in Virginia for the first time in over 20 years.
The loss in Kentucky will be seen as a setback for Mr Trump, who attempted to galvanise support for Mr Bevin at a campaign rally in Kentucky on Monday night.
In a speech to thousands of supporters, Mr Trump said a loss for Mr Bevin would be characterised as "the greatest defeat in the history of the world" by his critics.
Mr Beshear, he said, was "too extreme and too dangerous" to govern the state.
However polls showed Mr Bevin was one of the least popular governors in the country, following high-profile battles with unions and teachers.
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