Causing grief or affliction. (Merriam – Webster)
Full of grief: Cheerless. (Merriam – Webster)
Expressing grief: Sad. (Merriam – Webster)
Very sad. (Cambridge Dictionary)
Sorrowful; mournful; melancholy: (Dictionary.com)
Expressing sorrow; mournful. (Oxford Dictionaries)
A doleful expression, manner, or voice is depressing and miserable. (Collins Dictionary)
Meaning of doleful.
Indian Sad Doleful Stock Photos and Images.