(1) Background: Multiple acute concomitant cerebral infarcts (MACCI) are relatively uncommon. Data regarding the characteristics and outcomes of patients with MACCI are lacking. We, therefore, aimed to characterize the clinical features of MACCI. (2) Methods: Patients with MACCI were identified from a prospective registry of stroke patients admitted to a tertiary teaching center. Patients with an acute single embolic stroke (ASES) involving only one vascular bed served as controls. (3) Results: MACCI was diagnosed in 103 patients who were compared to 150 patients with ASES. MACCI patients were significantly older (p= 0.010), more often had a history of diabetes (p= 0.011) and had lower rates of ischemic heart disease (p= 0.022). On admission, MACCI patients had significantly higher rates of focal signs (p< 0.001), an altered mental state (p< 0.001) and seizures (p= 0.036). The favorable functional outcome was significantly less common in patients with MACCI (p= 0.006). In the multivariable analysis, MACCI was associated with lower chances of achieving favorable outcomes (odds ratio: 0.190, 95% CI: 0.070–0.502). (4) Conclusions: There are important differences in clinical presentation, comorbidities and outcomes between MACCI and ASES. MACCI is less often associated with favorable outcomes and could represent a more severe form of a stroke compared with a single embolic stroke.