Vancomycin, a glycopeptide antibiotic, is widely used for Gram-positive cocci or bacilli bacteria-induced serious infections. Although considered safe and effective, it still causes adverse events. Vancomycin-induced immune thrombocytopenia is a rarely reported adverse event, manifesting from asymptomatic thrombocytopenia to life-threatening bleeding. We underline a case of a 56-year-old male with a diabetic foot with an infected exudating purulent ulcer. He experienced a significant drop in platelet count after commencing vancomycin, and discontinuing vancomycin resulted in improved platelet count with positive vancomycin-induced anti-platelet antibodies. After ruling out other possible causes of thrombocytopenia, a presumptive diagnosis of vancomycin-induced thrombocytopenia was made.