Laryngomalacia (LM) and laryngeal cleft (LC) can independently cause dysphagia but rarely can occur concomitantly. We discuss the presentation, decision-making, and swallow outcomes following surgical correction of combined LM and LC. We present four patients with combined LM and an LC who underwent both primary supraglottoplasty (SGP) and laryngeal cleft repair (LCR). Each patient presented with recurrent choking or coughing with feeds. Stridor was only present in two patients. Patients with SGP saw the resolution of stridor when present, but dysphagia persisted in all four cases. LCR clinically and objectively resolved all symptoms of dysphagia. We found that flexible fiberoptic laryngoscopy is not always reliable at detecting combined pathology. Patients presenting with persistent dysphagia following SGP should be suspected of having interarytenoid pathology. We recommend a staged surgical approach with SGP before LCR.