The designation was chosen to honor Lloyd Owens, long-time Waukesha County Board Chairman.

Starting at an intersection with WIS 67 in the Town of Eagle, WIS 99 ran due east through an area of mixed agricultural land and residential subdivisions.

East of the intersection with Markham Road, the highway turned northward for about 1,000 feet (300 m) before returning to its eastward course on the north side of Eagle Spring Lake.

Running north of the Rainbow Springs Golf Resort, the highway continued into the community of Mukwonago.

The name was chosen to honor Lloyd Owens, former chairman of the Waukesha County Board at a time when the position was the most power in the county.