Bilateral breast tumors can be either synchronous or metachronous. Synchronous breast tumors account for 0.2-2% of all breast cancers and have a poorer prognosis when compared to metachronous and unilateral tumors. Phyllodes tumor, benign or malignant, may be rarely associated with ductal/lobular carcinoma in-situ and less often with invasive lesions. Here we report a rare case of synchronous malignant phyllodes tumor in left breast and invasive ductal carcinoma in right breast, which were diagnosed on routine mammogram and confirmed by histopathological evaluation. Extensive literature search showed two case reports of co-existence of benign phyllodes tumor and invasive ductal carcinoma as synchronous tumors in contralateral breasts. No case reports of malignant phyllodes tumor and invasive ductal carcinoma as synchronous tumors in distinct breasts was found and our case is the first one to be reported. Such synchronous co-existence warrants a strict follow up of the patient with further investigations to rule out another primary cancer and also screening of other family members.