This case report describes a rare presentation of double-vessel Spontaneous Coronary Artery Dissection (SCAD) in a 54-year-old male. One dissection occurred in a coronary artery with atherosclerotic plaque deposition, while the second vessel exhibited dissection without evidence of plaque deposition, trauma or iatrogenic manipulation such as percutaneous coronary intervention. The patient, a known hypertensive and dyslipidemic, had a prior diagnosis of heart failure with reduced ejection fraction (HFrEF). He presented with progressively worsening shortness of breath and orthopnea (two-pillow orthopnea for three years. An initial coronary angiogram was recommended due to a high suspicion of underlying coronary artery disease (CAD).Subsequent diagnostic workup revealed multisegmental wall motion abnormalities on 2D echocardiography with Doppler imaging. Laboratory tests, including electrolytes, were unremarkable. A follow-up coronary angiogram revealed mild to moderate CAD in the left anterior descending (LAD) artery and spontaneous coronary artery dissection involving both the LAD and the right coronary artery (RCA). The patient was managed conservatively with aspirin and discharged on a regimen of sacubitril/valsartan, ivabradine, trimetazidine, and rosuvastatin. As typically seen in SCAD cases, conservative medical management was preferred over invasive procedures such as PCI or coronary artery bypass grafting (CABG), which are reserved for select clinical situations.