James T. Kirk/Key dates/2260s

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|-| 2261=Breaks off relationship with Janet Wallace.
|-| 2263=Breaks off relationship with Areel Shaw.
|-| 2265=
* Takes the to the galactic barrier, the first Earth ship to do so in two hundred years.
* During the mission, is forced to kill close friend [[Gary Mitchell.
|-| 2266=
* Achieved first contact with the First Federation.
* Later that year, repels a Romulan incursion and destroys a Romulan Bird-of-Prey.
|-| 2267=
* Became the first Starfleet captain ever to stand court martial, charged with negligent homicide in the death of Benjamin Finney.
** Charges dismissed.
|-| 2268=
* Responsible for stealing a Romulan cloaking device during a covert Starfleet intelligence mission.
* Experiences amnesia and lived among the American Indians on Amerind where he wedded Miramanee.
|-| 2269=
* Diverts the asteroid-ship Yonada from destroying Daran V. 
* Nearly killed by Dr. Janice Lester with whom he'd had a year-long relationship years before.
* Trapped in a planet's past along with Spock and McCoy on a planet about to go supernova.
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