McKirk Timeline- TOS
This will probably be a bit empty, most of my TOS timelines will be because there's so much stuff to know about TOS that there's little to add
2255- Jim arrives on a medical starbase and meets Leonard McCoy (a surgeon who's just started his intensive care fellowship). They form a bond and start to miss each other when they're gone, this motivates them to keep in touch
2265- The Five Year Mission starts, a mission near to Capella IV gives Jim time to catch up with Bones
2266- The previous CMO retires, Jim asks Bones to replace him, Bones eventually agrees. They spend more time together and get closer due to them knowing each other previously. Feelings develop
2267- City on the Edge of Forever happens. Jim doesn't realise how in love with Bones he is, when he gets checked out he has dinner in private with him. They sit close on the sofa and share a kiss.
They don't do anything major about their feelings until after Mirror Mirror. Bones is touchy and acting worse than he says, Jim tells to him and lies him down in his lap and finds out how bad it was with Mirror!Spock. They enter a relationship
2268- Jim is hurt by how easily Bones decides to leave with Natira. They have their first big fight but talk about things and reach a new level of understanding.
2270- The Five Year Mission ends. Theu try to keep their relationship but fail when Jim doesn't tell him about his anxieties towards getting promoted and Bones doesn't tell him he's thinking of leaving Starfleet
2273- The Motion Picture happens, they get back together
2273-78- The Second Five Year mission starts. They share quarters and draw up ideas of their ideal life
2280- Jim leaves Starfleet, Bones does some more qualifications for xenomedicine. They get their ideal ranch in Georgia with stables, chickens and a vegetable patch. During the summer they sell veg and pies at the side of the road
2285- Wrath of Khan and the Search for Spock happens. Jim is almost inconsolable after Spock dies, Bones struggles to deal with his grief, Jim's struggles and Spock in his head
2286- The Voyage Home happens. Jim is struggling since Spock doesn't remember him, Bones struggles even more
2287- Bones' pain is made even worse when he confronts his past in the Final Frontier. Jim initially gets angry that Bones hasn't told him these things but Bones just breaks down and admits how hard it's been since he's felt overlooked during everything since Khan. They rekindle and go on a long holiday
2293- The Undiscovered Country happens, they barely get time to talk and process things when Jim goes missing. Bones struggles for years in depression, his friends help him to get out of it
2371- Bones and Julian Bashir resurrect Jim (explanation below), they catch up and Jim is shocked to see how different Bones is. Jim feels guilty that he 'left him behind' but this is quickly silenced by Bones
Edit: I forgot to add the explanation from Memory Beta (I know it's non canon but this is my canon), basically he did die and was returned to his universe but was resurrected by Romulans, who allied with the Borg and brainwashed him to want to kill Picard. Bones and Bashir managed to remove the Borg implant and Spock (with Picard) mind melded him to safety
I hope you enjoyed this!