Invasive facial fungal infections affect the orofacial soft tissues in immunocompromised patients and can cause significant morbidity and mortality. Primary infection occurs from direct inoculation of the skin surface, while secondary infection occurs from extension from an adjacent sinonasal process. The imaging features of secondary infection are similar to acute fulminant invasive fungal sinusitis with infiltration of the orofacial soft tissues in combination with sinonasal disease. However, primary infection can occur in the absence of sinonasal disease, making diagnosis challenging. We present two cases, one of primary and one of secondary invasive facial fungal infection. Careful scrutiny of the orofacial soft tissues in immunocompromised patients is necessary to detect invasive facial fungal infections so that appropriate surgical and medical therapies can maximize patient outcomes.