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Spontaneous coronary artery dissection (SCAD) is a rare cause of acute non atherothrombotic coronary syndrome. It predominantly affects female sex. Both diagnosis and therapeutic decision–making are challenging due to its unpredictable course and recurrence rate. We describe a case of a 50y old man with chest pain(CP), referred to our cathlab for primary percutaneous coronary intervention(PCI) through the Emergency Medical Service, with an anterior ST–segment elevation myocardial infarction(STEMI) detected on ECG. A type 2b SCAD starting from the Left Main(LM) involving proximal Left Anterior Descending (LAD) artery and circumflex artery(Cx) was detected. PCI with Drug–Eluting Stent(DES) implantation on LM and proximal LAD was deemed necessary due to ongoing ischemia and LM involvement. IntraVascular UltraSound(IVUS) on LAD and LM showed good stent deployment and confirmed a non–obstructive SCAD of Cx,left untreated. Patient was started with dual antiplatelet therapy and after 5 days in our cardiac intensive care unit(ICU) he was moved to cardiology unit. Few hours later he had recurrence of CP and an Inferior STEMI was detected. A progression of SCAD of the Cx with critical flow limitation in its proximal tract was found at coronary angiography. Then PCI with DES release was performed using a T and Small Protrusion technique on LM–LAD–Cx and cutting–balloon was used to fenestrate intima with a successful drainage of the intramural hematoma (IH) in the distal portion. Our case represents an uncommon presentation of SCAD, as STEMI involving a male patient. In a recent large cohort of SCAD patients only 10% were men. Male SCAD patients are younger, have less frequently prior MI, depression, emotional stress triggers and are less likely to have associated fibromuscular dysplasia. More often they report physical stress triggers and a more subtle clinical presentation. Conservative management remains the mainstay of treatment in the absence of ongoing ischemia, hemodynamic instability, or LM involvement. When PCI is indicated, it is often associated with an unfavorable course (difficult wiring of the lesion, propagation, and potential milking of the IH along the vessel).Cutting balloon technique has been increasingly used in the interventional approach to SCAD. Several questions remain unanswered about appropriate antithrombotic regimen, duration of ICU observation and the opportunity to perform coronary imaging to review the disease prior to a safe discharge.