March 4-5, 1861 – Two very clean strangers show up in Sunrise Wyoming looking for Samuel Colt. (Frontierland)
1954 – John Winchester is born. (What Is And What Should Never Be)
December 4, 1954 – Mary Winchester (Nee Campbell) is born. (year - Children Shouldn’t Play With Dead Things, date – What Is And What Should Never Be)
-The article on the plane crash in the DjinnWish-verse in WIAWSNB is dated December 5th, Newspaper report on events the day AFTER they happen, which means that the plane crash actually occurred on December 4th, therefore when Dean watches (I’m assuming the 11 o’clock) news after celebrating Mary’s birthday in the DjinnWish-verse and they say that it is one year anniversary of the crash, it would mean that it is December 4th
April 24, 1967 – The Impala rolls off the assembly line in Janesville, Wisconsin. (Swan Song)
October 1972 - 8 Nuns are disemboweled at St. Mary's Convent in Ilchester, Maryland. (Lucifer Rising)
-The newspaper Sam reads this from is dated October 16th, 1972.
April 30th, 1973 - John Winchester buys a 1967 Impala on the recommendation of a stranger. (In The Beginning)
May 2nd, 1973 - John Winchester proposes to Mary Campbell (In The Beginning)
- Samuel and Deanna Campbell are murdered (In The Beginning)
One night around April/May 1978 – Anna attempts to kill John and Mary Winchester. They end up with no memories of the encounter or the two Hunters that helped them. At this time, John and Mary live at the address 485 Robintree, Lawrence, Kansas. It is not the same house as the Sam and Dean’s childhood home. (The Song Remains The Same)
-Mary is pregnant with Dean, but it is still very early in the pregnancy.
January 24th 1979 - Dean is born
May 2nd, 1983 - Sam is born
Between May and November 1983 – John and Mary have a fight and John leaves home for a few days. (Dark Side of the Moon)
November 2nd 1983 - Mary Dies
1985/1986 – John takes Dean shooting for the first time.
April 7th, 1985 - Jo Harvelle is born (Hunters Log - S2 DVD special features)
March 1985 - a meteor is seen over Kentucky. (Heaven and Hell)
December 1985 - Anna Milton is born. (Heaven and Hell)
~1989/1990 - A Shtriga almost kills Sam in Fort Douglas, Wisconsin (Something Wicked)
-(I've also seen this year referenced as 1988 with a citation to John Winchester's Journal)
January 1990 - John Winchester investigates a series of grave robbings in Windom, Minnesota. (Jump the Shark)
September 29th, 1990 - Adam Milligan is born. (Jump the Shark)
December 25, 1991 - Sam and Dean spend Christmas alone in Broken Bow, Nebraska, while John is on a hunt. (A Very Supernatural Christmas)
Summer 1994 – Sam and Dean spend a portion of the summer being looked after by Donna, a babysitter (and maid at the Mayflower) in Housatonic, Massachusetts, while their father hunts. On one occasion, John is gone for two weeks. It is the summer before Sam enters 6th grade, and he assigns himself a summer reading list. Dean possibly has a crush on Donna. (Swap Meat)
-Year estimated by assuming Sam was 11 when he entered 6th grade.
Unknown – One or both boys go to the Cleveland Botanical Gardens on a field trip. (Dark Side of the Moon)
November 24th, 1994 (Thanksgiving) – Sam has his first traditional Thanksgiving dinner at his friend Stephanie’s house. He has been attending a school called McKinley for two weeks. (Dark Side of the Moon)
1995 - Sam wins a division championship soccer trophy (Bad Day at Black Rock)
- While Sam waits in the car, Dean kills something (most likely a werewolf) with a silver-arrow to the heart while on a hunt with his father and "embraces the life" of a hunter.(Bloodlust)
May 16th, 1995 - William (Bill) Anthony Harvelle is killed while on a hunt with John.(Hunters Log - S2 DVD special features)
July 4th, 1996 – Sam and Dean “burned down that field” when they set off their own fireworks display. (Dark Side of the Moon)
Unknown (presumably when Sam is a teenager) – Sam runs away for two weeks and lives in Flagstaff, Arizona. He befriends a dog, who he names Bones. Dean fears he is dead and gets in trouble for Sam leaving “on his watch.” (Dark Side of the Moon).
~1996/1997 - at the age of 13, Sam experiences a brief phase where he wants to be a magician. (Chriss Angel Is A Douchebag)
Summer 1997 - The Winchesters hunt a werewolf (After School Special).
-There is an inconsistency in After School Special, because it informs us that it is 1997, and Sam says it's November, but in the High School there are "class of 97" banners everywhere, which would indicate that the graduating class is going to graduate in June 1997, which would make it November 1996. That being said, the caption on the episode itself informs us that it is 1997.
November 1997 - Sam and Dean attend Truman High in Fairfax, Indiana, for 3 or 4 weeks, while John is on a hunt that was originally supposed to be 2 weeks but ended up taking longer than expected. (Dean is in 12th Grade. It is the third school they have attended since September.) (After School Special)
-There is an inconsistency in After School Special, because it informs us that it is 1997, and Sam says it's November, but in the High School there are "class of 97" banners everywhere, which would indicate that the graduating class is going to graduate in June 1997.That being said, the caption on the episode itself informs us that it is 1997.
~1998 - Sam is a mathlete (Metamorphosis).
~September 1998 - Dean takes a roadtrip alone, while Sam and John are in Orlando, Florida, hunting a banshee. He meets Lisa Braeden. (The Kids Are Alright)
Late May or Early June, 1999 – Ben Braeden is born. (The Kids Are Alright)
2002 - Sam leaves for Stanford.
2002/2003 - Adam Milligan meets John Winchester. (Adam states that he is 12 at the time) (Jump the Shark).
Thanksgiving 2003 - Sam's friend Brady returns from holiday and begins to get into drugs. Sam attempts to help. (The Devil You Know).
A Spring either in 2003 or 2004 - Dean dates Cassie Robinson in Athens, Ohio, for a few weeks, while she finishes up her senior year of college (at Ohio University). Personal Opinion - Spring 2003. (Route 666)
Sometime in early 2004 - Sam begins dating Jessica, after being introduced by his friend Brady. (Route 666 - Sam said he dated Jessica for a year and a half) (The Devil You Know - Sam tells us that Brady introduced him to Jess.)
Summer 2005 - John teaches Adam Milligan to drive using the Impala. (Jump the Shark)
- Adam claims he was 15 when John taught him to drive in the Impala, but that's impossible given that Dean had sole possession of the car while Adam was 15. So, John must have taught him the summer he was 14.