On four occasions in the last two centuries, great powers have conducted military withdrawals out of Afghanistan. Each time, these powers left mechanisms in place that protected their national interests. Despite the perception that both the British and Soviets suffered disastrous defeats, each still retained enough leverage to attain some of the objectives for which they went to war in the first place. The US-led North Atlantic Treaty Organization (NATO) coalition is poised to make the fifth such withdrawal by the end of 2014. Can it also achieve similar strategic objectives? Each of these four departures from Afghanistan occurred in a geopolitical environment of competition between great powers: the Great Game and the Cold War. External competition will surely continue to influence post-2014 Afghanistan, as multiple regional and world powers have national interests at stake. This paper examines the lessons from the four previous great power withdrawals, in the context of Afghanistan’s long-running, competitive geopolitical environment. It also considers which of the lessons remain applicable in the post-2014 regional geopolitical environment.