The Summer of '78 (June 1978) - Father's Day, with expectant parents John and Mary.
Merry Christmas, Darling (1978) - John and Mary, captured in a sweet moment a month before Dean's birth.
What Child Is This (1983) - John and the Wee!Chesters, with flashbacks of Mary. On Sammy's first Christmas, John looks back at Dean's previous Christmases.
If Santa Were My Daddy (1984) - John and Wee!Dean. It's a tough question: "Daddy, are you Santa?"
Hide and Seek (1985) - There's someone whispering. Someone terrible. John and the wee ones.
The Baby Jesus Gets All the Applause (1986) - Wee!Dean and Pastor Jim. Dean has a snit over 3-year-old Sammy being tapped to play Jesus -- who's a baby, thank you very much.
Santa's Little Helper (1987) - While John is wrangling with a nitwit clerk in Auto Parts, 8-year-old Dean finds himself a job. John and the boys.
One Too Many (Dec 1987) - John, Dean, Sammy. John and the boys are stranded at a diner during a blizzard -- and there's something out there in the snow.
Pilgrim (November 1988) - At Thanksgiving time, Dean sets out to right a wrong, with Sammy in tow. Outsider POV.
White Christmas (1988) - Sammy's yearning for snow -- in Florida. Wee!Dean and Sam.
Treasures (1989) - John and the boys. Sam makes a special gift for Dean -- then has to leave it behind when the family moves on.
If Only In My Dreams (1990) - John, the boys, OFC. The Winchesters find refuge on Christmas Eve with a woman John saved from an angry spirit.
Family Ties (1991) - John, Bobby, and the boys. Dean's in trouble at school, and Bobby comes to his rescue.
Nothing But the Truth (1991) - John returns to the motel, post A Very Supernatural Christmas (the flashbacks). John, Sam, Dean.
Ghosts of Christmas Past (1992) - John at the Roadhouse with Ellen and wee!Jo.
Because It's Christmas (1993) - Dean gets a little carried away with the holiday decorating. John and Dean.
O Tannenbaum (1994) - Dean and Sam, and Sam's new saucer sled. (And John.)
Gremlins (1995) - The boys take over a hunt as a Christmas gift for John and run into a little unexpected trouble. Dean and Sam.
Let There Be Lights (1996) - Dean, Sam, OCs. Hanging Christmas lights for an elderly neighbor is a bigger job than Dean anticipated.
Your One True Love (Jan 1997) - John prepares a special gift for Dean's 18th birthday.
No Room at the Inn (1997) - Dean, Sam, OCs. The boys share motel rooms with a group of stranded college students...and a lot of beer.
Go Tell It on the Mountain (1998) - John and the boys take refuge in a mountain cabin during a hunt.
Not With a Bang But a Whimper (1999) - Dean drunk-dials Bobby on Christmas Eve.
The Gift of the Winchester (2000) - Dean and Sam. Dean gives till it hurts to provide Sam with a special Christmas present.
Room 509 (May 2001) - Dean, Sam. Sam's 18th birthday isn't exactly a success.
I Saw Mommy Kissing Dean-a-Claus (2001) - Dean's a Santa for the new millennium, helping out at a women's shelter. Dean and Sam.
Blue Christmas (2002) - John and Dean head to Pastor Jim's for the holidays.
A Nightmare Before Christmas (2003) - A distressed Sam (at Stanford) is the recipient of some Secret Santa gifts. From...who??
Fifty (2004) - John and Dean, on John's 50th birthday.
Deck the Halls (2004) - Sam and Jess attend a Christmas party with friends.
Sunshine (On My Shoulders) (Jan 2005) - Sam, Jess. Sam helps Jess celebrate her 21st birthday.
Brothers (2005) - Dean and Sam, flashback to John with OCs. A storage unit fic - John gets an unusual glimpse into his sons' lives.
You Are My Sunshine (Nov 2005) - Dean and Sam on the road post-Wendigo, leading up to Thanksgiving.
Love, It Is a Razor (Jan 2006) - Dean and Sam, on Dean's -- and Jessica's -- 27th birthday.
God Rest Ye Merry, Gentlemen (2006) - The boys (and their good friend Jack Daniels) watch infomercials.
What Are You Doing New Year's Eve? (2006) - Sam, Bobby and Dean - and the real purpose of Dean's amulet.
Revisionist History (April 2007) - Dean and Sam. Dean remembers that picture of the graduation Sam didn't have. (WIAWSNB)
Mary, Did You Know? (2007) - Sam, Ruby, Dean (by phone). Sam seeks some peace and quiet in church to sort out what the YED (and Ruby) told him about his mother.
Just Another Auld Lang Syne (2007) - Dean and Sam stargaze on New Year's Eve.
If the Fates Allow (Thanksgiving) (Nov 2008) - Sam, Jess. Sam has a visitation from Jess -- but is it really her?
If the Fates Allow (Christmas) (Dec 2008) - Mary, Dean, Castiel. Dean's hit rock bottom, so the angels secure some help in setting him back on track.
Pie (June 2009) - Bobby, Dean, Sam. Father's Day, with Bobby and the boys.
Than Never To Have Loved At All (2009) - On Thanksgiving, Dean struggles to deal with the events of episode 5.10. Dean, Sam, Bobby, and Castiel. Spoilery for 5.10.
Found Object (Dec 2009) - Dean, Sam, Missouri Mosely. The boys receive a startling gift from Missouri at Christmastime.
Birthday Boy - Dean, Sam. Drabbles looking at Dean's major birthdays through the years.
Resurrection and the Light (2011) - Hope Verse - Dean, Morgan, Lizzie. Dean joins his girls at church on Easter Sunday.
Blackbird (2011) - Dean, Sam. The boys have a bit of downtime on Halloween, and meet a young Trick-or-Treater.
Distraction (With Pie) (2011) - Dean, Sam. Sam attempts to explain Kwanzaa to Dean -- and there's pie.
Of Then, And Now (2011) - Dean, Sam. Unfulfilled wishes from past Christmases bring the boys to a Toys R Us at holiday time.
Silent Night (2012) - Hope Verse - Dean, mentions of Sam, Bobby, Ellen, Jo, various OCs from my future 'verse. The Winchesters share the Donahues' family Christmas in the Adirondacks.
My Grown-Up Christmas List (2012) - Hope Verse - Dean, Morgan and Lizzie on Christmas morning.
Trick or Treat (2013) - Dean, Morgan, Lizzie. Lizzie prepares for trick-or-treating with her dad.
LARP the Night Away (2013) - Dean, Morgan. Dean gets a reward for trick-or treating with the little kids.
Let There Be Pink (2013) - Hope Verse - Dean, Sam. Dean's stressed out by Lizzie's request for an unusual Christmas gift.
His Father's Son (Nov 2024) - Hope Verse - Dean, RJ. Dean and his son bond on Thanksgiving.
Just Us (Dec 2025) - Hope Verse - Dean, RJ. Dean and his son have some fun on Christmas Day.
Worthy (Nov 2031) - Hope Verse - Dean, RJ. RJ frets about writing a Veterans' Day paper.
Ours (2035) - Hope Verse - Sam, Dean, Connie. Sam and Connie's wedding day.
The Peacemaker (Dec 2038) - Hope Verse - Dean, Campbell. Grandpa Dean soothes his granddaughter's wounded spirits with a special Christmas gift.
One Hundred (2050) - Bobby, Dean, Sam. Bobby Singer turns 100.