ia pernah menjalin hubungan yang panjang dengan johnny depp (4 tahun), penyanyi band soul asylum david pirner (3 tahun), dan matt damon (3 tahun).
hubungannya dengan johnny depp adalah yang paling terkenal.
(selama berpacaran, depp membuat tato yang bertuliskan "winona forever," di lengannya yang kemudian dimodifikasi menjadi "wino forever" setelah hubungan mereka berakhir).
menurut berbagai sumber, dari beberapa kolom tabloid dan gosip, winona ryder pernah berkencan dengan bintang film daniel day-lewis, david duchovny, val kilmer, chris noth, jimmy fallon, dan christian slater; dengan musisi conor oberst (bright eyes), ryan adams, evan dando (vokalis the lemonheads), adam duritz (vokalis the counting crows), franz hemingbeck, dave grohl (nirvana, the foo fighters), page hamilton (helmet), beck hansen, jay kay, rhett miller, pete yorn dan john s.
great balls of fire!
myra gale lewis
welcome home, roxy carmichael
nominated  golden globe award for best supporting actress
night on earth
bram stoker's dracula
wilhelmina "mina" murray/elisabeta
francis ford coppola
the age of innocence
golden globe award for best supporting actress nominated  academy award for best supporting actress nominated  bafta for actress in a supporting role
the house of the spirits
josephine "jo" march
nominated  academy award for best actress
how to make an american quilt
dr. katz, professional therapist
looking for richard
the larry sanders show
also executive producer
autumn in new york
strangers with candy
juan j. campanella
babe bennett/pam dawson
the day my god died
voice, producer, documentary film
the heart is deceitful above all things
the darwin awards
a scanner darkly
sex and death 101
gillian de raisx/death nell
the last word
the private lives of pippa lee
j. j. abrams
when love is not enough: the lois wilson story
john kent harrison
pre-production, tv film
penghargaan dan nominasi
1990 independent spirit award best female lead heathers nbr award best supporting actress mermaids showest award female star of tomorrow - young artist award best young artist starring in a motion picture great balls of fire! 1991 golden globe best performance by an actress in a supporting role in a motion picture mermaids 1992 saturn award best actress edward scissorhands sant jordi award best foreign actress (mejor actriz extranjera) 1993 saturn award best actress bram stoker's dracula mtv movie award best kiss nbr award best supporting actress the age of innocence 1994 academy award best actress in a supporting role bafta film award best actress in a supporting role golden globe best performance by an actress in a supporting role in a motion picture mtv movie award best kiss reality bites sefca award best supporting actress the age of innocence 1995 academy award best actress in a leading role little women chlotrudis award best actress kcfcc award best actress 1996 mtv movie award best kiss how to make an american quilt 1997 showest award female star of the year - 1998 saturn award best supporting actress alien resurrection blockbuster entertainment award favorite supporting actress - sci-fi 2000 blockbuster entertainment award favorite actress - drama girl, interrupted peter j.
owens award - - star on the walk of fame motion picture - 2001 razzie award worst screen couple autumn in new york 2002 teen choice award film - choice actress, comedy mr. deeds 2003 razzie award worst actress 2009 scream award best cameo star trek