The Collaborative International Dictionary of English v.0.48:

Condole \Con*dole"\, v. i. [imp. & p. p. Condoled; p. pr. &
   vb. n. Condoling.] [L. condolere; con- + dolere to feel
   pain, grieve. See Doleful.]
   To express sympathetic sorrow; to grieve in sympathy; --
   followed by with.
   [1913 Webster]

         Your friends would have cause to rejoice, rather than
         condole with you.                        --Sir W.
                                                  Temple.
   [1913 Webster]

The Collaborative International Dictionary of English v.0.48:

Condole \Con*dole"\, v. t.
   To lament or grieve over. [R.]
   [1913 Webster]

         I come not, Samson, to condole thy chance. --Milton.
   [1913 Webster]

WordNet (r) 3.0 (2006):

condole
    v 1: express one's sympathetic grief, on the occasion of
         someone's death; "You must condole the widow"

The Devil's Dictionary (1881-1906):

CONDOLE, v.i.  To show that bereavement is a smaller evil than
sympathy.