1994
- First announcement of the FreeDOS Project (then "PD-DOS"). (29 June 1994) ~ comp.os.msdos.apps
- FreeDOS changes its name from "PD-DOS" to "Free-DOS." (16 July 1994) ~ comp.os.msdos.apps
- First "Alpha" release: FreeDOS officially releases the Free-DOS Alpha 1 distribution. (16 September 1994)
- First article about FreeDOS ~ University of Wisconsin-River Falls: UWRF Student Voice (December 1994)
- First book about FreeDOS: The FreeDOS Kernel by Pat Villani. (6 January 1996) ~ R+D Books
- FreeDOS drops the hyphen, changes its name from "Free-DOS" to "FreeDOS."
1997
- First article about FreeDOS in popular press ~ DOS World Magazine (March 1997)
1998
- First "Beta" release: FreeDOS officially releases the FreeDOS Beta 1 "Orlando" distribution. (25 March 1998)
2000
- First third-party redistribution: Italian magazine DEV distributes FreeDOS Beta 4 (February 2000
2001
- First conference talk about FreeDOS (Jim Hall) ~ SSGRR-2001 (August 2001)
2002
- First third-party book about FreeDOS: The Universal Command Guide by Guy Lotgering ~ Wiley
- First major PC install: Dell ships FreeDOS install CDs with n-series computers (August 2002)
2004
- Major milestone: FreeDOS turns 10 years old (29 June 2004)
2006
- First "1.x" release: FreeDOS officially releases the FreeDOS 1.0 distribution. (3 September 2006)
2012
- FreeDOS officially releases the FreeDOS 1.1 distribution. (2 January 2012)
2014
- Major milestone: FreeDOS turns 20 years old (29 June 2014)
2016
- FreeDOS officially releases the FreeDOS 1.2 RC1 distribution. (31 October 2016)
2019
- Major milestone: FreeDOS turns 25 years old (29 Jun 2014)

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