Background: Dysphagia is a common complication after stroke and is associated with the development of pneumonia. This study aimed to summarize the relationship between dysphagia and pneumonia in post-stroke patients. Materials and Methods: Articles published up to November 2021 were searched in the PubMed, Embase, Cochrane library, and Scopus databases. Studies that investigated the development of pneumonia in acute stroke patients with and without dysphagia were included. The methodological quality of individual studies was evaluated using the Risk Of Bias In Non-randomized Studies-of Interventions tool, and publication bias was evaluated using a funnel plot and Egger's test. Results: Of 5,314 studies, five studies were included in the meta-analysis. The results revealed that the incidence of pneumonia was significantly higher in the dysphagia group than in the non-dysphagia group (OR 9.60; 95% CI 5.75–16.04; p < 0.0001; I2 = 78%). There was no significant difference in the mortality rate between the two groups (OR 5.64; 95% CI 0.83–38.18; p = 0.08; I2 = 99%). Conclusion: Dysphagia is a significant risk factor for pneumonia after stroke. The early diagnosis and treatment of dysphagia in stroke patients are important to prevent stroke-associated pneumonia.