June 1st, 1983 - Born to Mitch and Natalie Winters

September 27th, 1998 - Car accident

Late July, 1999 - Carrie meets Bobby for the first time

Late September, 1999 - Carrie meets Sam and Dean for the first time

September 28th, 1999 - Sam and Dean leave Bobby's

October 16th, 1999 - Sam and Dean return

October 17th, 1999 - John hits Carrie

October 18th, 1999 - Carrie and Dean's first kiss

October 19th, 1999 - Carrie meets Wolfe for the first time

October 20th, 1999 - John leaves

October 28th, 1999 - John returns

October 29th, 1999 - Dean, Sam and Carrie get arrested after getting into a fight at the diner / Pastor Jim and Caleb arrive / Pastor Jim and Carrie remember each other from months ago

October 30th, 1999 - Pastor Jim and Carrie talk about the past / John tortures and kills a demon in the basement / Carrie hears screaming

October 31st, 1999 - John leaves with Pastor Jim and Caleb

November 15th, 1999 - Dean pranks Carrie and Sam, and the prank war begins

November 16th, 1999 - Carrie pranks Dean

November 17th, 1999 - John returns / Dean puts Nair in Sam's shampoo causing his hair to fall out / John ends the prank war

Sometime in December, 1999 - Carrie finds out that Wolfe has cancer

Sometime in December, 1999 - Bobby and Carrie bake together / they talk / they have a flour war

December 31st, 1999/January 1st, 2000 - Wolfe dies

June 18th, 2000 - Bobby dies / John takes in Carrie / Carrie spends the time before her and Sam leave for Stanford with the Winchesters

June 1st, 2001 - Carrie's 18th birthday

July 3rd, 2001 - Carrie and Sam receive their Stanford acceptance letters, but choose to hide them from John and Dean

August 27th, 2001 - Dean discovers Carrie and Sam's Stanford acceptance letters

August 31st, 2001 - Sam and John's big argument / Sam walks out / Carrie goes with him

September 2nd, 2001 - Dean drops Carrie and Sam off at Stanford