Dr. Cruickshank received his medical degree in 1970 from State University of New York, Downstate Medical College, in Brooklyn, New York. He completed his internship in medicine and surgery in 1971 and his residency in general surgery in 1972 at St. Vincent's Hospital Center in New York City. He completed a second residency in urology in 1976 at State University of New York, Downstate Medical Center, in Brooklyn, New York.

Dr. Cruickshank is a diplomate of the National Board of Medical Examiners and is certified by the American Board of Urology. He is also certified in extracorporeal shock wave lithotripsy. Dr. Cruickshank is a fellow of the American College of Surgeons, the Suffolk Academy of Medicine, and the New York Academy of Medicine.

Dr. Cruickshank is an assistant professor of clinical urology in the Department of Urology, School of Medicine, State University of New York at Stony Brook. He is a member of numerous professional societies, including the American Urological Association, the American Medical Society, the Suffolk Medical Society, the New York Academy of Sciences, the New York State Society of Surgeons, the American Association of Clinical Urologists, and the Brooklyn, Queens, and Long Island Urological Society.

Dr. Cruickshank has been the recipient of several awards, including being listed in the Castle Connolly Guide as one of the best doctors in the New York Metropolitan area in 1994, 1996, and 1998.