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Jeffrey Grey was educated at the Australian National University and the University of New South Wales, where he completed his doctorate in history in 1986. He began his teaching career in the Department of History in the old Faculty of Military Studies at RMC Duntroon in 1983 after six years in the Commonwealth Public Service. He was appointed to a lectureship in the Department of History at ADFA in 1988 after a short stint with the Historical Documents Project at the Department of Foreign Affairs.
He was promoted steadily through the course of the 1990s, achieving the rank of full professor in 2004. He has served a term as convenor of the Graduate Program in Defence Studies (1998-2000), and has taught in that program since first appointment. The author or editor of more than twenty books and numerous other shorter publications, he has served on the editorial board of several journals (including the Journal of Military History) and has acted as an historical advisor to film and television makers on several occasions. For over a decade he has provided expert advice to the Department of Veterans' Affairs on matters arising under the Veterans Entitlements Act.
Grey is a trustee of the Society of Military History in the United States, the first person outside North America to hold such a position. In northern academic years 2000-2002 he held the Major General Matthew C. Horner Chair of Military Theory at the Marine Corps University in Quantico, Virginia. His continuing interest in professional military education is reflected in his long-standing involvement in teaching and advising at the Australian Defence College at Weston, ACT. In March 2004 he was appointed Director of the UNSW Defence Studies Forum.