- Reference Stardate 2/1000: Starfleet Intelligence later learns that the Nelson class scout U.S.S. Valdez, captured by the Klingon Empire during the war a decade earlier, was destroyed during this time. The Klingons had been using the Valdez along their coreward border at the time of its destruction.
- Reference Stardate 2/1001: Starfleet Intelligence later confirms that, at this time, the Romulan Star Empire begins using Klingon-built Stormbird class cruisers along the Romulan Neutral Zone.
- Reference Stardate 2/0806: Due to tectonic instability, Ceti Alpha VI, which shared a binary orbit with Ceti Alpha V, explodes. The effect alters Ceti Alpha V's orbit slightly, transforming it from a luxurious garden world into an inhospitable desert.
- Stardate Unknown (23 January): (VAN #5, Chapter 1)
- Stardate 3715.3 (approx. 29 January): The crew of the Enterprise visits a mysterious and deadly paradise planet which they discover is controlled by a machine called Vaal.
- Reference Stardate 2/1001.30 (30 January): In the Triangle, the world of Penchan II becomes the fourth member of the Imperial Klingon States. Penchan is vital to the future existence of the IKS, due to its vast deposits of raw materials such as dilithium, allowing the IKS to begin rebuilding its worn-out fleet.
- Stardate Unknown: A transporter mishap slips Captain Kirk and his companions into a parallel universe, where the Enterprise serves a barbaric Empire instead of the Federation.
- Stardate Unknown (18-26 February): (VAN #5, Chapters 2-13)
- Stardate 3842.3/Reference Stardate 2/0902: (approx. 16 March): While transporting dignitaries to an important peace conference, the Enterprise is pursued by a mysterious vessel and an assassin is discovered among the passengers. (TOS 44) The question of Coridan's admission to the United Federation of Planets is settled by the inspired oratory of Ambassador Sarek of Vulcan. Meanwhile, the first of a series of Romulan/Klingon non-aggression and technological exchange treaties are signed.
- Stardate Unknown (22-23 March): (VAN #5, Chapters 14-15)
- Stardate 3950.1 (approx. 24 April): Captain Una steals the Transfer Key while visiting the U.S.S. Enterprise NCC-1701, in an attempt to rescue her comrades from the alternate universe where they have been trapped since 2249. Soon after, the Key is stolen by a Romulan Tal Shiar agent who had infiltrated the Enterprise crew.
- Reference Stardate 2/1005: Originally issued by the Tellarite Planetary Government, and later adopted by the Federation in 2281, the Federation Peace Medal commends an individual who has set a personal example of fostering peace, mutual respect, and cooperation among divergent races.
- Stardate 4040.7 (approx. 17 May): Captain Kirk and a landing party are forced to fight in gladiatorial games on a planet modeled after the Roman Empire.
- Stardate Unknown: A Romulan ship uses the stolen Transfer Key in an attempt to disrupt Federation/Klingon peace talks on Centaurus by transporting several members of both delegations, including Ambassador Sarek and Councilor Gorkon, into an alternate universe.
- Stardate Unknown: Following the destruction of the Romulan ship and the recovery of the Transfer Key, the U.S.S. Enterprise NCC-1701 travels from Centaurus to the disputed world of Usilde to rescue all of the people who have become trapped in the alternate universe.
- Stardate Unknown (26-30 May): (VAN #5, Chapters 16-18)
- Stardate Unknown (2-5 June): (VAN #5, Chapters 19-23)
- Reference Stardate 2/0003: Starbase 27, constructed near the Federation's border with the Klingon Empire, assumes operational status.
- Stardate 4202.9/Reference Stardate 2/0802 (approx. 26 July): After losing his entire crew to an alien planet-eating machine, Commodore Matthew Decker pulls rank on Captain Kirk in order to play a game of cat-and-mouse with the mechanical adversary. His efforts to destroy the menace place the Enterprise in grave danger. In a tactic later known as the Kirk Defense, and following Decker's self-sacrificial example, the Enterprise crew disables the Doomsday Machine by setting the Constellation's engines for self-destruct, exploding the starship inside the Doomsday Machine.
- Stardate 4211.4 (approx. 29 July): Captain Kirk must decide how to save a primitive people from the technological interference of the Klingons.
- Stardate Unknown (30-31 July): (VAN #5, Chapters 27-29)
- Stardate Unknown (1-3 August): (VAN #5, Chapters 30-33)
- Stardate Unknown (19 August): (VAN #5, Chapters 34-35)
- Stardate Unknown (24 August): (VAN #5, Chapter 36)
- Stardate 4307.1 (approx. 2 September): The crew of the Enterprise encounters an energy-draining space creature.
- Stardate Unknown (9-10 September): (VAN #5, Chapters 37-49)
- Stardate Unknown (12-14 September): (VAN #5, Chapters 50-52)
- Stardate 4372.5 (approx. 26 September): Captain Kirk hosts a spoiled princess, who must bring peace to a star system at war.
- Stardate 4385.3 (approx. 1 October): For trespassing on an alien world, Captain Kirk and his companions are forced to re-enact the famous shoot-out at the O.K. Corral with themselves cast as the losing side.
- Stardate 4513.3 (approx. 16 November): Captain Kirk and the crew have another run-in with Harry Mudd, this time finding him as the king of a planet of androids.
- Stardate Unknown (19 November): (VAN #5, Chapter 53)
- Stardate 4523.3 (approx. 20 November): Tribbles—purring, limbless, and fertile—disrupt the colonization of a disputed planet between the Klingon Empire and the Federation.
- Stardate 4598.0 (approx. 17 December): The Enterprise visits a planet with a violent culture based on America's 1920s prohibition era.
- Stardate Unknown (28-29 December): (VAN #5: "#5, Chapters 54-60)
Captain Kirk's five-year mission was established to have begun in 2265 in the Star Trek: Voyager episode "Q2". The Star Trek] episode "The Menagerie, Part I" further establishes that Spock served under Captain Pike for 11 years, and that it had been 13 years since the events of "The Cage," meaning that Stardate 3012.4 fell two years into Kirk's command. The episode "Charlie X" further added weight to this, establishing both Stardate 1533.1 and the Earth date of Thanksgiving, which falls on 23 November in 2265. As the stardates ranged from the mid-1000s to the low 3000s in the first season and continued to increase at approximately 1000 per season afterward, it seems logical to conclude that the first season spanned nearly two years, and later seasons one each, with the second season chronicling the 3000s, the third season the 4000s and 5000s, and the Animated Series the 5000s. If Captain Kirk's command began on or about Stardate 1000, this would put the end of the five year mission on or about Stardate 6000, shortly after the end of the Animated Series. Using these dates as a reference point, the following can be established:
- Stardate 1000 fell on 13 May 2265.
- The range for Stardates each year is from X636 to Y635 (e.g., 1636 to 2635)
- This places "The Menagerie" (Stardate 3012.4) on 18 May 2267, at the beginning of Kirk's third year in command of the Enterprise
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- Wheeler, Wm. John with McLimore, Guy W. Jr., Poehlein, Greg K., and Tepool, David F. "Cadet's Orientation Sourcebook." Star Trek: The Role Playing Game, Book 2004A. FASA Corporation, 1983.
- Cox, Greg. Legacies, Book 1: Captain to Captain. Star Trek. Pocket Books, June 2016.
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- Mack, David. Legacies, Book 2: Best Defense. Star Trek. Pocket Books, July 2016.
- Ward, Dayton & Dilmore, Kevin. Legacies, Book 3: Purgatory's Key. Star Trek. Pocket Books, August 2016.
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- Roddenberry, Gene (Executive Producer/Teleplay). "A Private Little War." Star Trek, Season 2, Episode 16. Directed by Marc Daniels. Story by Jud Crucis. Desilu Productions, 2 February 1968.
- Roddenberry, Gene (Executive Producer). "The Immunity Syndrome." Star Trek, Season 2, Episode 19. Directed by Joseph Pevney. Written by Robert Sabaroff. Desilu Productions, 19 January 1968.
- Roddenberry, Gene (Executive Producer) and Freiberger, Fred (Producer). "Elaan of Troyius." Star Trek, Season 3, Episode 2. Directed by John Meredyth Lucas. Written by John Meredyth Lucas. Paramount Pictures Corporation, 20 December 1968.
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- Roddenberry, Gene (Executive Producer). "I, Mudd." Star Trek, Season 2, Episode 12. Directed by Marc Daniels. Written by Stephen Kandel. Desilu Productions, 3 November 1967.
- Roddenberry, Gene (Executive Producer). "The Trouble With Tribbles." Star Trek, Season 2, Episode 13. Directed by Joseph Pevney. Written by David Gerrold. Desilu Productions, 29 December 1967.
- Roddenberry, Gene (Executive Producer). "A Piece of the Action." Star Trek, Season 2, Episode 20. Directed by James Komack. Written by David P. Harmon (Story and Teleplay) and Gene L. Coon (Teleplay). Desilu Productions, 12 January 1968.