Synonyms for Woeful:

adj.

all (adjective)
woebegone.
dejected (adjective)
disconsolate, heartbroken, anguished, lachrymose, dolorous, disheartened, overcome, despondent, dejected, miserable, plaintive, joyless, sullen, pensive, anxious, discouraged, moody, melancholy, morose, contemplative, glum, mournful, depressed, gloomy, dreary, downhearted, despairing, dispirited, wistful, blue, sad, grim.
doleful (adjective)
doleful, painful.
painful (adjective)
cruel, aching, hurtful, unpleasant, grievous, troublesome, smarting, uncomfortable, painful, excruciating, irritating, crushing, burdensome, stabbing, Besetting, horrendous, piercing, inflaming, distressful, tormenting, biting, anguishing, aggravating, harrowing, throbbing, annoying, bitter, Irksome, offensive, trying, miserable, wrenching, stinging, withering, acute, grueling, cutting, insufferable, disagreeable, unbearable, Gnawing, Torturing., Cramping, bothersome, arduous, oppressive, sore, agonizing, chafing, odious, severe.
terrible, sad (adjective)
doleful, grievous, grim, anguished, cruel, disconsolate, sorrowful, wretched, deplorable, gloomy, plaintive, miserable, mournful.
woebegone (adjective)
woebegone.

n.

sadly, utterly, thorough, unspeakable, downright, utter, such as it is, hopelessly. doleful, lugubrious, rueful. regrettable. woeful (noun)
execrable, inferior, wretched, sorrowful, deplorable, miserable, woebegone.

Other synonyms:

lugubrious, regrettable. rueful. doleful. Other relevant words:
doleful, inferior, lugubrious, bleak, regrettable, rueful, execrable, wretched, sorrowful, woebegone, deplorable.

Usage examples for woeful

  1. Howe sent a request to Washington desiring three days cessation of arms to take care of the wounded and bury the dead, which was refused: what a woeful tendency war has to harden the human heart against the tender feelings of humanity. – Stories of New Jersey by Frank Richard Stockton
  2. For the favourite of Lord Ormont to stoop from her place beside him- ay, but women do; heroes have had the woeful experience of that fact. – The Complete Project Gutenberg Works of George Meredith by George Meredith