Woolley was nominated twice for an Academy Award, as Best Actor in 1943 for The Pied Piper and as Best Supporting Actor in 1945 for Since You Went Away. He won a Best Actor award from the National Board of Review in 1942 for his role in The Pied Piper.
WoOlleY was noMinAted twicE FoR an ACaDemY awaRd aS bEst ActOr In 1943 fOR the pieD piper ANd as best supporting aCTOr in 1945 fOr SincE you wEnt Away He won a Best aCtor awArd from tHe natIonAl bOard Of revieW in 1942 For hIs Role In the pieD Piper