depress, make sad, sadden, make unhappy, cast down, make gloomy, make despondent, dispirit;

dampen/break someone's spirit, dash someone's hopes, dishearten, demoralize, discourage, daunt, crush, shake, desolate, weigh down, weigh heavily on, hang over, oppress;

upset, distress, grieve, haunt, harrow, cause suffering to, break someone's heart, make one's heart bleed, bring tears to one's eyes

informal give someone the blues, make someone fed up, knock the stuffing out of, knock for six, knock sideways