Dr. Woolliscroft received his MD degree from the University of Minnesota in 1976. He completed his Internal Medicine residency at the University of Michigan and joined the Medical School faculty in 1980 in the Department of Internal Medicine.

Dr. Woolliscroft is an internationally recognized medical educator. He has played major roles in medical student, resident and fellow education at the University of Michigan. He has also served to establish standards for education and accreditation at a national level for medical schools and graduate medical education. He has held leadership positions in the Association of American Medical Colleges Group on Educational Affairs and the Clerkship Directors in Internal Medicine. He has also served on the National Board of Medical Examiners.

His research interests in medical education have resulted in numerous peer reviewed publications and invited presentations and visiting professorships across the US and internationally. Dr. Woolliscroft was selected as the first Josiah Macy, Jr. Professor of Medical Education, an endowed professorship awarded through a national competition in 1996. He held this position through December 2000. In January 2001, he received a second endowed professorship, the Lyle C. Roll Professor of Medicine recognizing his work in enhancing the practice of medicine through education.

At the University of Michigan he has served in many capacities ranging from course director to Associate Chair in the Department of Internal Medicine, to Chief of Clinical Affairs of the University of Michigan Hospitals. He currently serves as the Executive Associate Dean of the University of Michigan Medical School.