This case report highlights a unique co-presentation of two rare infections, Lemierre’s syndrome and Ludwig angina in a patient, caused by a polymicrobial infection involving unusual pathogens, Streptococcus anginosus and Candida dubliniensis. Ludwig angina is a severe submandibular infection known for its rapid spread, posing a risk of airway obstruction due to edema. On the other hand, Lemierre’s syndrome typically arises as a complication of a peritonsillar abscess, wherein the infection extends into the parapharyngeal and carotid spaces and even reaches the internal jugular vein. This case report describes a 50-year-old white male patient who presented with left submandibular swelling, extending to the anterior neck, lower left facial droop, and severe trismus. A neck CT scan revealed substantial dental caries, thrombophlebitis, and multiple submental abscesses. The patient underwent three incision and drainage procedures for the abscesses, excision, and ligation of the left internal jugular vein and common facial vein, as well as dental tooth extractions. Microbial cultures from the abscesses identified Streptococcus anginosus and Candida dubliniensis, while blood cultures revealed Prevotella buccae. Notably, Fusobacterium necrophorum, the typical causative agent of Ludwig angina, was not isolated. Treatment involved a six-week course of ceftriaxone, metronidazole, and micafungin, followed by six months of fluconazole. The patient showed improvement in trismus, neck swelling, and pain; however, he continued to exhibit a lower left facial droop. This case highlights important clinical insights, emphasizing the importance of promptly recognizing Ludwig’s angina and its potential progression to Lemierre’s syndrome.