Dr Whitfield graduated from Monash University in 1998.  He trained in general surgery in Western Australia and South Australia from 2005-2008.  He was awarded Fellowship with the Royal Australasian College of Surgeons in 2009.

Dr Whitfield undertook post-Fellowship training in breast and endocrine surgery at The Queen Elizabeth Hospital in Adelaide in 2009.  In 2010 he was appointed Chief Surgical Resident at the Royal Adelaide Hospital and received additional post-Fellowship training in breast surgery, oncoplastics and breast reconstruction, endocrine surgery and surgical oncology / melanoma surgery.  In 2011 Dr Whitfield completed an oncoplastic breast Fellowship in Edinburgh, UK.

Dr Whitfield has worked as a staff specialist general surgeon on the Breast, Endocrine & Surgical Oncology Unit at the Royal Adelaide Hospital and as a Visiting Surgeon at BreastScreen SA since 2012.  He has an interest in medical education and is the current supervisor of general surgery training at the Royal Adelaide and Deputy Chair of the SA & NT Training Committee of the Board in General Surgery.

Dr Whitfield commenced private practice in 2014.