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Background: Intensive lifestyle intervention (ILI) is essential for diabetes management. The Weight Achievement and Intensive Treatment (Why WAIT) program is a 12-week multidisciplinary weight management program that has been implemented in real-world clinical practice since 2005 and has shown long-term maintenance of weight reduction for 5 and 10 years. During the COVID-19 pandemic, the program went virtual using telemedicine and mobile health applications. Aims: This retrospective pilot study aims to evaluate the effectiveness of a virtual model of an already established and successful in-person program for diabetes and weight management since 2005. Methods: We evaluated 38 patients with diabetes and obesity enrolled in the Why WAIT program between February 2019 and December 2020. Sixteen participants were enrolled in virtual program (VP) and were compared with 22 participants who completed the latest two physical programs (PPs) before COVID-19. We evaluated changes in body weight, A1C, blood pressure (BP), and lipid profile after 12 weeks of ILI. Results: Body weight decreased by −7.4 ± 3.6 kg from baseline in VP compared with −6.8 ± 3.5 kg in PP ( p = 0.6 between groups). A1C decreased by −1.03% ± 1.1% from baseline in VP, and by −1.0% ± 1.2% in PP ( p = 0.9 between groups). BP, lipid profile, and all other parameters improved in both groups with no significant difference between them. Conclusion: Virtual multidisciplinary ILI is as effective as the in-person intervention program in improving body weight, A1C, BP, and lipid profile, and in reducing the number of anti-hyperglycemic medications. Results from our study suggest that scaling the Why WAIT program in a virtual format to a larger population of patients with diabetes and obesity is feasible and is potentially as successful as the in-person program.