The Collaborative International Dictionary of English v.0.48:

Woeful \Woe"ful\, Woful \Wo"ful\, a.
   1. Full of woe; sorrowful; distressed with grief or calamity;
      afflicted; wretched; unhappy; sad.
      [1913 Webster]

            How many woeful widows left to bow
            To sad disgrace!                      --Daniel.
      [1913 Webster]

   2. Bringing calamity, distress, or affliction; as, a woeful
      event; woeful want.
      [1913 Webster]

            O woeful day! O day of woe!           --Philips.
      [1913 Webster]

   3. Wretched; paltry; miserable; poor.
      [1913 Webster]

            What woeful stuff this madrigal would be! --Pope.
      [1913 Webster] Woefully

WordNet (r) 3.0 (2006):

woeful
    adj 1: affected by or full of grief or woe; "his sorrow...made
           him look...haggard and...woebegone"- George du Maurier
           [syn: woebegone, woeful]
    2: of very poor quality or condition; "deplorable housing
       conditions in the inner city"; "woeful treatment of the
       accused"; "woeful errors of judgment" [syn: deplorable,
       execrable, miserable, woeful, wretched]

Moby Thesaurus II by Grady Ward, 1.0:

146 Moby Thesaurus words for "woeful":
   abominable, affecting, afflictive, aggrieved, anguished, arrant,
   atrocious, awful, base, beastly, beneath contempt, bitter,
   blameworthy, bleak, brutal, calamitous, careworn, cheerless,
   comfortless, contemptible, crushed, cut up, deep-troubled,
   dejected, deplorable, depressed, depressing, depressive, desolate,
   despicable, detestable, dire, discomforting, disconsolate,
   disgusting, dismal, dismaying, dispirited, distressful,
   distressing, doleful, dolorific, dolorogenic, dolorous, downcast,
   downhearted, dreadful, dreary, dumb with grief, egregious,
   enormous, fetid, filthy, flagrant, foul, fulsome, grave,
   grief-stricken, griefful, grieved, grievous, gross, harrowed,
   hateful, heart-stricken, heart-struck, heartbreaking, heartsick,
   heinous, horrible, horrid, in grief, in the dumps, inconsolable,
   infamous, joyless, lamentable, loathsome, lousy, low-spirited,
   lugubrious, miserable, monstrous, mournful, moving, nasty,
   nefarious, noisome, notorious, obnoxious, odious, offensive,
   on the rack, outrageous, overcome, painful, pathetic, piteous,
   pitiable, pitiful, plaintive, plangent, plunged in grief, poignant,
   racked, rank, regrettable, reprehensible, repulsive, rotten,
   rueful, ruthful, sad, saddening, scandalous, schlock, scurvy,
   shabby, shameful, sharp, shocking, shoddy, sordid, sore, sorrowed,
   sorrowful, sorrowing, squalid, stricken, suicidal, tearful,
   terrible, too bad, tortured, touching, unclean, uncomfortable,
   unfortunate, unprecedented, vile, villainous, woebegone, worst,
   worthless, wretched, wrung