A 60-year-old woman, recently diagnosed with invasive lobular breast carcinoma, presented with oppressive chest pain radiating to the left shoulder, lasting 15–30 minutes and resolving spontaneously. The electrocardiogram demonstrated sinus tachycardia, ventricular ectopy, including couplets, and a known left bundle branch block, in the absence of ST-T segment abnormalities. The troponin levels were elevated, rising from 1,442 to 13,396 ng/L in 1 hour. Transthoracic echocardiography revealed dyssynchrony of the interventricular septum with marked apical hypokinesia and basal segment hypercontractility. Based on the clinical presentation, characteristic wall motion abnormalities and elevated troponin levels in the absence of ischemic ECG changes, a preliminary diagnosis of Takotsubo syndrome (TTS) was made. Recent huge emotional distress related to the diagnosis of a breast lesion, further supported this diagnosis. To exclude obstructive coronary artery disease, coronary angiography was performed which revealed no critical stenoses in the epicardial coronary arteries but demonstrated a spontaneous coronary artery dissection (SCAD) in a distal coronary branch. T o further investigate, a cardiac magnetic resonance was performed and revealed a dilated left ventricle with globally reduced systolic function (LVEF 44%) and regional wall motion abnormalities, including hypokinesia of the apical and mid-ventricular segments, associated with septal dyssynchrony. Furthermore, CMR demonstrated T2 hyperintensity involving the mid-apical anterior wall, tissue characterization (LGE) involving the mid-apical anterior wall, consistent with sub-acute myocardial infarction in the distal left coronary artery territory, and myocardial edema. The prevalence of TTS is around 1-2% of all acute coronary syndromes, while SCAD accounts for approximately 1-4% of all acute myocardial infarctions. This case illustrates the concomitant occurrence of Takotsubo syndrome and spontaneous coronary artery dissection in a patient with newly diagnosed breast cancer. Both conditions are uncommon, and their association is exceedingly rare, particularly in the cardio-oncology setting. The overlap between these entities highlights the importance of systematic multimodal assessment to avoid misdiagnosis and to guide optimal management. Increased awareness of this association may contribute to improved risk stratification and tailored treatment in oncologic patients presenting with acute chest pain.