Background: Evidence-based guidelines for determining dietary management in dogs with megaoesophagus are lacking. Objectives: This study looked to compare oesophageal clearance times (ECT) of liquid and two food consistencies using a contrast videofluoroscopy feeding evaluation, and to assess if recommendations made based on findings could improve regurgitation and quality of life in dogs with congenital megaoesophagus. Methods: Twenty-one dogs with congenital megaoesophagus and nine healthy dogs received liquid, slurry, and meatball diets containing barium while in an upright position. Follow-up was performed to determine response to recommendations. Results: Healthy dogs had significantly shorter median ECT for all consistencies (p < 0.001). In the megaoesophagus group, ECT varied by consistency and individual. The number of dogs in the megaoesophagus group with complete clearance was four (median ECT 10 min) for liquid, five (median ECT 5 min) for slurry, and two (median ECT 5 and 30 min, respectively) for meatballs. Partial clearance was seen in 11 dogs (median clearance 25%) with liquid, seven with slurry (median clearance 50%), and five with meatballs (median clearance 60%). Recommendations included altering current medications (13/21 dogs), diet consistency (6/21), time upright (12/21), water delivery (21/21), and adding activity (7/21). Regurgitation episodes/week decreased significantly from 5.5 to 2.5 (p < 0.001) at follow-up 3–5 weeks post-evaluation, with 95% of owners reporting improvement in quality of life. Seventy percent were alive 46–777 days after last recheck. Three dogs died from megaoesophagus associated complications (median survival 461 days after diagnosis). Conclusions: The findings of this study suggest that a videofluoroscopic feeding evaluation may help guide management of dogs with congenital megaoesophagus.