Source : Webster's Revised Unabridged Dictionary (1913)

Doleful \Dole"ful\, a.
   Full of dole or grief; expressing or exciting sorrow;
   sorrowful; sad; dismal.

         With screwed face and doleful whine.     --South.

         Regions of sorrow, doleful shades.       --Milton.

   Syn: Piteous; rueful; sorrowful; woeful; melancholy; sad
        gloomy; dismal; dolorous; woe-begone. - {Dole"ful*ly},
        adv. -- {Dole"ful*ness}, n.

Source : WordNet®

doleful
     adj : filled with or evoking sadness; "the child's doleful
           expression"; "stared with mournful eyes"; "mournful
           news" [syn: {mournful}]