A 56-year-old man was admitted to intensive care with septic shock, multiple facial abscesses and thrombophlebitis of the right internal jugular vein with extensive intracranial extension. A diagnosis of Lemierre syndrome due to Streptococcus anginosus was made and treatment initiated with high-dose ceftriaxone and metronidazole, along with surgical debridement. His admission was complicated by raised intraocular pressures and visual loss requiring bilateral canthotomies. Despite therapeutic anticoagulation with enoxaparin, he also developed an ischaemic basal ganglia infarct. After a prolonged and complex hospital stay, the patient was later readmitted with an intracerebral abscess requiring surgical excision and a second course of antibiotics. This case highlights the value of early recognition of this rare but potentially life-threatening condition, considerations around anticoagulation and antibiotic decisions, and the importance of close multidisciplinary follow-up even after discharge from hospital.