Dr. Pineless received his Doctorate in Osteopathic Medicine from the Chicago College of Osteopathic Medicine in 1981. He performed a rotating medical internship at the Chicago Osteopathic Hospital and the Olympia Fields Osteopathic Medical Center, from 1981 to 1982. He then completed his neurology residency at the VA Hines Hospital, Hines, IL, and at Loyola University Medical Center, Maywood, IL, from 1982 to 1985. Dr. Pineless served on the faculty of the Chicago College of Osteopathic Medicine as an Assistant Professor of Medicine in the Section of Neurology from 1985 to 1986. He is listed in Who's Who in Medicine and Healthcare, and Who's Who in America. Dr. Pineless has been in practice in the Orlando area since 1986. Dr. Pineless was the president of the Florida Osteopathic Medical Association (FOMA) from 2012–2013. Dr. Pineless also serves as Clinical Assistant Professor of Neurology at Florida State University (FSU) College of Medicine. Dr. Pineless is certified by the American Osteopathic Board of Neurology and Psychiatry, and the American Society of Neurorehabilitation. He is an active member of numerous professional medical societies, including the American Osteopathic Association, the American Academy of Neurology, the American College of Neuropsychiatrists, the National Headache Foundation, and the Seminole County Medical Society. Dr. Pineless has been helping to advance the field of neurology through publishing and presenting professional articles on a variety of topics in neurology at numerous professional assemblies. He is on the active staff of ORHS South Seminole Hospital in Longwood. Dr. Pineless is a former Chief of Staff of Florida Hospital East Orlando, a past member of the Board of Trustees of Florida Hospital, and has been named Physician of the Year by Florida Hospital East Orlando on several occasions. In 2007, Dr. Pineless was elected by his peers as a Fellow by the American College of Neuropsychiatrists. He has also been chosen by his peers on numerous occasions as one of Orlando Magazine's Top Doctors.