サイモン・チェスターマン（Simon Chesterman、1973年 - ）は、オーストラリア出身の法学者。シンガポール国立大学法学部教授。専門は国際法。
メルボルン大学卒業。ローズ奨学生としてオックスフォード大学に留学し、博士号取得。ニューヨーク大学教授を経て、2012年から現職。また国際連合人道問題調整事務所やルワンダ国際戦犯法廷での実務経験を有する。
著書 Just war or just peace?: humanitarian intervention and international law, Oxford University Press, 2001. You, the people: the United Nations, transitional administration, and state-building, Oxford University Press, 2004. One Nation Under Surveillance: A New Social Contract to Defend Freedom Without Sacrificing Liberty, Oxford University Press, 2011.
共著 Studying Law at University, with Clare Rhode, Allen & Unwin, 1998. Law and practice of the United Nations: documents and commentary, Simon Chesterman, Thomas M. Franck, David M. Malone, Oxford University Press, 2008.
編著 Civilians in war, Lynne Rienner Publishers, 2001. Making States Work: State Failure and the Crisis of Governance, edited by Simon Chesterman, Michael Ignatieff and Ramesh Thakur, United Nations University Press, 2005. From mercenaries to market: the rise and regulation of private military companies, edited by Simon Chesterman and Chia Lehnardt, Oxford University Press, 2007. Secretary or general?: the UN Secretary-General in world politics, edited by Simon Chesterman, Cambridge University Press, 2007. After Mass Crime: Rebuilding States and Communities, edited by Simon Chesterman, Béatrice Pouligny and Albrecht Schnabel, United Nations University Press, 2007. Private Security, Public Order: The Outsourcing of Public Functions and Its Limits, edited by Simon Chesterman and Angelina Fisher, Oxford University Press, 2009.