OK, here's some highlights from my TOS chronology (Concentrating on Kirk, Spock, and McCoy to keep it to a reasonable length):
Jan. 20, 2220 - Leonard H. McCoy is born in Atlanta, Georgia on the planet Earth. His father is David McCoy.
March 3, 2220 - Montgomery Scott is born in Aberdeen, Scotland, Earth.
2229 - Vulcan Ambassador Sarek marries teacher Amanda Grayson of Earth.
March 26, 2230 - Spock is born to Sarek and Amanda in the city of ShiKahr on the planet Vulcan.
2231 - George Samuel Kirk is born to George and Winona Kirk. (Conjecture. The script for
Star Trek (2009) describes Kirk’s brother as being three years older than him.)
March 22, 2234 - James T. Kirk is born to Lt. Commander George Kirk and Lt. Winona Kirk in Riverside, Iowa.
2237 - Spock undergoes his
kahs-wan ritual one month early, attempting to survive for ten days without food, water, or weapons on Vulcan's Forge. Spock's pet sehlat I-Chaya is mortally injured when it follows him. (“Yesteryear.”)
2237 - Spock and T'Pring are telepathically bonded in a ritual Vulcan ceremony arranged by their parents. ("Amok Time.")
2237 - Christopher Pike (age 18) enters Starfleet Academy.
2237 - Leonard McCoy (age 17) enters medical school at the University of Mississippi. (Conjecture based on DS9: “Trials and Tribble-ations.”)
2237 - Leonard McCoy meets Trill Emony Dax when she judges a gymnastics competition at Ole Miss. (DS9: “Trials and Tribble-ations.” Dax recalls that,
“I met him when he was a student at Ole Miss… My host at time was Emony. She was on Earth judging a gymnastics competition. I had a feeling he’d become a doctor… he had the hands of a surgeon.”)
Jan. 2240 - Montgomery Scott (age 19) enters Starfleet Academy mid-term. (DC ST v1 Annual #3.)
2241 - Christopher Pike (age 22) graduates from Starfleet Academy at the top of his class. (Conjecture based upon
Burning Dreams.)
2243 - Montgomery Scott (age 23) graduates from Starfleet Academy. In his Starfleet career he will ship out on a total of 11 vessels, including freighters, cruisers and Starships. (TNG: "Relics.")
2244 - Joanna McCoy is born to Leonard (age 24) and Jocelyn McCoy. (Conjecture. 21 years before 2265, assuming that Joanna graduated college that year, as stated in DC ST v1 Annual #1 (1985):
“All Those Years Ago…”)
2244 - Dr. Richard Daystrom invents duotronic computer technology and is awarded the Nobel and Zee-Magnees prizes. Dr. Daystrom’s computer systems become the basis for the main computers of the starship
Enterprise. ("The Ultimate Computer.")
2245 - The USS
Enterprise, NCC-1701, is launched from the San Francisco Yards facility in orbit around Earth, under the command of Captain Robert April.
2245 - Leonard McCoy (age 25) graduates from medical school. ("The Pirates of Orion." Kirk comments that McCoy has been in medicine for 25 years.)
2245 - The Battle of Donatu V is fought near Sherman’s Planet, in a region disputed by the Klingon Empire and the United Federation of Planets. The results are inconclusive. ("The Trouble With Tribbles.")
2246 - Christopher Pike (age 28) is promoted to Commander. (
Burning Dreams.)
2246 - James T. Kirk (age 12) is one of the survivors of the massacre on Tarsus IV. (“The Conscience of the King.”)
2246 - Spock (age 16) declines placement in the Vulcan Science Academy, enlisting in Starfleet against his father's wishes. He takes the accelerated two-year course of study for Vulcans. Sarek and Spock do not speak to each other for the next 18 years. (“Journey to Babel”,
Star Trek (2009),
Vulcan's Glory.)
2248 - Spock (age 18) begins one year of working cadet cruises aboard various ships. (
Vulcan's Glory.)
2249 - Spock (age 19) graduates from Starfleet Academy. Amanda attends her son’s graduation ceremony on Earth. (
Vulcan's Glory. Amanda states that it has been
“five years” since she saw Spock at his graduation.)
2249 - Ensign Spock begins three years as an assistant science officer on a space cutter in the Sol system. (
Vulcan's Glory.)
2250 - James T. Kirk (age 16) enters Starfleet Academy with the assistance of Mallory. ("The Apple.")
2250 - James Kirk meets Gary Mitchell at Starfleet Academy. (Kirk refers to Gary as
"a man I've known for 15 years" in "WNM." Elizabeth Dehner says that they've been friends since Gary entered the Academy.)
2250 -
Enterprise Commodore Robert April (age 55) retires from Starfleet and becomes Federation Ambassador at large. (“The Counter-Clock Incident.” Kirk states that April has been an ambassador
“for the past 20 years.”)
2250 - Captain Christopher Pike (age 32) assumes command of the USS
Enterprise.
2251 - Dr. Leonard McCoy (age 31) leads a mass-inoculation program on Dramia II. Shortly after McCoy's team leaves, an Auroral Plague kills almost the entire population of Dramia II. (“Albatross.” Stated to be
“19 years ago.”)
2252 - Spock (age 22) is promoted to Lieutenant (Junior Grade) and serves on the USS
Artemis as third officer & science officer under Captain Daniels. (
Vulcan's Glory)
2252 - James T. Kirk sees Ruth for the last time before 2267. ("Shore Leave." Kirk tells the simulacrum of Ruth:
“You haven’t aged. It’s been 15 years.”)
2253 - Leonard McCoy (age 33) begins a romantic relationship with the future Nancy Crater (age 25). ("The Man Trap." McCoy remarks that Nancy
“looks exactly as I knew her 12 years ago… like a girl of 25,” implying that he met her and/or began a relationship with her that long ago.)
2253 - James T. Kirk (age 19) barely escapes with his life when five of his Academy classmates die attempting the Kolvoord Starburst during shuttlepod maneuvers. (
The Autobiography of James T. Kirk)
Late Dec. 2253 - Spock (age 23) is promoted to Lieutenant & transfers to the USS
Enterprise as second officer and science officer. (
Vulcan's Glory. 11 years, 4 months & 5 days before Kirk takes command of the Enterprise (April 2265). The novel begins on a
“late December day.")
2254 - James T. Kirk (age 20) graduates from Starfleet Academy.
2254 - Ensign Kirk begins serving on the USS
Republic, NCC-1371, under Captain Garrovick. (“Court Martial.” Captain Garrovick commanding the
Republic is my conjecture, based upon Kirk’s statement in “Obsession” that Garrovick
“was my commanding officer from the day I left the Academy. One of the finest men I ever knew.”)
2254 - "The Cage"
2254 - Onboard the USS
Republic, Ensign James T. Kirk logs that his friend Ben Finney left a circuit open that could have led to the destruction of the ship. Finney draws a reprimand and is moved to the bottom of the promotion list. (“Court Martial.”)
2255 - Ensign James T. Kirk transfers to the USS
Farragut, NCC-1647, alongside Captain Garrovick. It is Kirk's first deep-space assignment. ("Obsession.")
2255 - Leonard McCoy’s relationship with the future Nancy Crater comes to an end. Nancy marries Professor Robert Crater shortly thereafter. (“The Man Trap.” McCoy states in 2265,
“We walked out of each other's lives ten years ago.” It is my conjecture that McCoy’s relationship with Nancy was an extramarital affair. Since Kirk has not met Nancy Crater a decade later, he evidently did not know, or was not in touch with, McCoy at this time.)
2255 - Leonard McCoy (age 35) and Jocelyn McCoy divorce. Believing that there is nothing left for him on Earth after his divorce, Leonard McCoy enlists in Starfleet. (Conjecture based upon
Star Trek (2009), where McCoy is recently divorced in 2255.)
2255 - James T. Kirk (age 21) is promoted to Lieutenant (Junior Grade). (Conjecture. Assumes that Kirk spent one year at the rank of Ensign after graduating from the Academy in 2254.)
2255 - Lt. J.G. James T. Kirk commands his first planetary survey on the planet Neural, a technologically unsophisticated Class-M planet. (“A Private Little War.” Kirk refers to himself as,
“the brash young Lieutenant Kirk on his first planet survey,” and states that he left the planet
“thirteen years ago.”)
2257 - James T. Kirk (age 23) is promoted to full Lieutenant. (Conjecture. Assumes he spent 10 months to two years at the rank of Lt. (J.G.).)
2257 - The USS
Farragut is destroyed, along with half of its crew, by a mysterious cloud creature while exploring planet Tycho IV. Lt. Kirk, manning phaser control, blames himself for not firing on the creature sooner. ("Obsession.")
2257 - Lt. James T. Kirk is accepted into Starfleet Command School, also teaching courses to midshipmen. Gary Mitchell aims a “little blonde lab technician” at Jim Kirk, in the hopes of getting his friend to loosen up. Kirk and Carol Marcus soon fall in love and begin a romantic relationship that lasts for the next several years. (Conjecture based upon "WNM.")
March-April 2258 - Lt. James T. Kirk makes three attempts to successfully complete the
Kobayashi Maru scenario at Starfleet Command School. He is finally beats the test when he reprograms the simulation to make it possible to rescue the ship. He is awarded a commendation for original thinking. (TWOK. Time placement is my conjecture.)
2258 - James T. Kirk graduates from Starfleet Command School.
2259 - James T. Kirk (age 25) is promoted to Lieutenant Commander. (Conjecture. Assumes he spent two years at the rank of Lieutenant.)
Dec. 31, 2259 - James Kirk proposes to Carol Marcus on New Year’s Eve. (Conjecture.)
Early 2260 - James Kirk and Carol Marcus make plans to get married. (Conjecture.)
April 2260 - Carol Marcus calls off her engagement to Jim Kirk when she discovers that she is pregnant. (Conjecture.)
Sept. 3, 2260 - David Marcus is born to Carol Marcus. He is the son of James T. Kirk, although his father will not learn of his existence for some time. (Conjecture.)
2261 - Lt. Commander James T. Kirk (age 27) begins serving as first officer on the USS
El Dorado, NCC-1722. (Conjecture based upon William Rotsler’s
Star Trek II Biographies.)
2261 - During his leave time, Spock (age 31) participates in a botany project at M.I.T. requiring the services of a Class A-7 computer expert. During the project, Botanist Leila Kalomi falls in love with him, but he is unable to return her feelings. (“This Side of Paradise”,
Strangers from the Sky.)
2262 - James T. Kirk has a romantic relationship with the future Janet Wallace. (“The Deadly Years.” Janet Wallace reminisces that it has been
“6 years, 4 months, and an odd number of days” since she and Kirk have last seen each other.)
2262 - James T. Kirk (age 28) is promoted to Commander. (Conjecture. Assumes he spent three years at the rank of Lt. Commander.)
2263 - James T. Kirk has a romantic relationship with Starfleet attorney Areel Shaw. (“Court Martial.” Areel Shaw reminisces that it has been
“4 years, 7 months and an odd number of days” since she and Kirk have last seen each other. McCoy has not met Areel Shaw prior to 2267, indicating that he and Kirk are probably not serving together at this time. I have no idea what Kirk is doing to these women that makes them count the days since they've seen him last.)
2263 - Commander James T. Kirk (age 29) assumes command of the USS
Saladin, NCC-500. (Conjecture based upon William Rotsler’s
Star Trek II Biographies.)
2264 - Spock (age 34) visits his home on Vulcan. (“Journey to Babel.” Amanda chides Spock,
“you haven't come to see us in four years.” I’ve interpreted this visit to be an attempt by Amanda to break Sarek & Spock’s silence, since adding 4 years to their 18-year estrangement allows Spock’s service record to stretch back to 2246, which jibes with D.C. Fontana’s novel
Vulcan’s Glory.)
April 2265 - James T. Kirk (age 31) is promoted to Captain. He assumes command of the USS
Enterprise. (Note that Kirk makes Captain a year sooner than Pike.)
Then TOS takes place from 2265-2270, as I detailed in my earlier post.
I personally like this, because it gives Kirk and Spock fairly realistic career progressions and lets them serve on a number of ships besides the
Enterprise. (Although Kirk certainly could have fit in a few more ships here & there, and perhaps even a starbase posting, just for variety's sake. This would also make his romances with Areel Shaw & Janet Wallace easier.) It also keeps Kirk from being too much of a
wunderkind who makes Captain at age 29. I decided that him having a command before the
Enterprise made a lot of sense, but decided to keep that while he was a Commander, so that his appointment to the
Enterprise could be his first command as Captain.
I decided to shift Kirk's time as an instructor at the Academy to after the 2257
Farragut incident, as it made sense to me that such a devastating event would shake young Kirk's confidence and make him want to retreat back to Earth for a while. So I figure he split his time between Command School and teaching classes. This also made the timeline of his relationship with Carol Marcus make a LOT more sense.
After his breakup with Carol, Kirk is alone for a couple of years, until he meets Janet.
I haven't settled on a few dates in McCoy's biography yet, like his marriage to Jocelyn and the death of his father David. STV doesn't really give us any hints as to exactly when McCoy's father died. I have a vague memory of some timeline saying that McCoy's marriage was in 2243, though. If I had to guess when McCoy & Kirk first met, I'd say it was either in 2254 (McCoy says that Bailey reminds Kirk of himself "11 years ago" in "The Corbomite Maneuver" - An unusually specific figure unless they knew each other then) or in 2255, shortly after McCoy's divorce, in similar circumstances as to what we saw in
Star Trek (2009).
Piecing together Kirk's career ascent is notoriously tricky, especially when one takes licensed fiction into account
Boy, ain't that the truth!

I now try to draw my conclusions primarily from the show and the movies, and leave the novels and the comics to fill in gaps if they don't substantially contradict anything.
FWIW I have him serving on no less than nine ships between 2257 and 2263 while he climbs the ladder from Lt. Cmdr and 2nd officer to Commander and XO to Captain.
Wow, that's a lot! I was figuring four or five, with him assuming several positions over the years (navigator, science officer, assistant engineer, first officer, etc.) to be as well-rounded as possible before he becomes captain.
(...I prefer the version of this from DC Comics' ST Annual #1; I've never cared for McIntyre's Enterprise: The First Adventure)
Same here. I'm with the DC version of Kirk's first mission on the
Enterprise all the way.
...I consider "WNM" (and about ten novels as well) to fall during a more-than-year-long period before the official "Five Year Mission" begins.
I haven't quite gotten there yet. I can see the logic in all the arguments that WNM isn't a part of the official 5YM (travel time, crew & uniform differences, no opening narration in the credits), but I still like it to be a part of the 5YM, interstellar distances be damned.
Star Trek always fudged the travel time and distances involved, anyway.
"Space Seed" I have bumped into mid-2267, to keep it 15 (okay, less than 16) years from STII: TWOK
Same here. I had to fudge it a bit. But I take solace that I at least didn't change two clear references to 15 years to 18!
2292 (Jun-Aug) - STVI:TUC
...I know it's conventional to put this in 2293, but that doesn't seem to me to fit. For one thing, McCoy has been CMO for 27 years (since 2265). For another, it makes sense to me to have some reasonable gap in between this and the next movie
Same here, for the same reasoning. I never liked the idea of the Ent-B launching in the exact same year the Ent-A gets decommissioned. I figure a gap of one year makes sense. You've got to give Kirk a little time to get bored in retirement, after all. My only difference is that I put the main events of TUC in May so that Captain Sulu could be free to attend Demora's graduation from Starfleet Academy.
2292-93 - Nine novels (my ordering: Assignment: Eternity, Best Destiny, Sarek, Mind Meld, Shadows on the Sun, Last Roundup, Fearful Summons, Ashes of Eden, and Federation).
I tend to discount the "Here's the
real final mission" aspects of these novels, as I personally don't think that any of them are better than the last adventure we saw in TUC. That was the last mission of Kirk's crew, full stop.