What If?, subtitled The World's Foremost Military Historians Imagine What Might Have Been, is a collection of twenty essays and thirteen sidebars dealing with counterfactual history. It was published by G.P. Putnam's Sons in 1999, ISBN 0-399-14576-1, and this book as well as its two sequels, What If? 2 and What Ifs? of American History, were edited by Robert Cowley. It was later combined with What If? 2 to form The Collected What If?.
- "Infectious Alternatives" by William H. McNeill
- "No Glory That Was Greece" by Victor Davis Hanson
- "Conquest Denied" by Josiah Ober
- "Furor Teutonicus: The Teutoburg Forest, A.D. 9" by Lewis H. Lapham
- "The Dark Ages Made Lighter" by Barry S. Strauss
- "The Death That Saved Europe" by Cecelia Holland
- "If Only It Had Not Been Such a Wet Summer" by Theodore K. Rabb
- "The Immolation of Hernán Cortés" by Ross Hassig
- "The Repulse of the English Fireships" by Geoffrey Parker
- What if the Spanish Armada had successfully landed in England?
- "Unlikely Victory" by Thomas Fleming
- "What the Fog Wrought" by David McCullough
- "Ruler of the World" by Alistair Horne
- What if Napoleon Bonaparte had chosen to do several things differently?
- "If the Lost Order Hadn't Been Lost" by James M. McPherson
- "A Confederate Cannae and Other Scenarios" by Stephen W. Sears
- What if the Civil War had not lasted as long as it did? (Five ways are presented here.)
- "The What Ifs of 1914" by Robert Cowley
- "How Hitler Could Have Won The War" by John Keegan
- "Our Midway Disaster" by Theodore F. Cook, Jr.
- "D Day Fails" by Stephen E. Ambrose
- What if the Allied invasion of Europe had failed in June 1944?
- "Funeral in Berlin" by David Clay Large
- What if American and not Soviet forces had taken Berlin in 1945?
- "China Without Tears" by Arthur Waldron
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