Background: Bariatric procedures are effective options for weight loss (WL) in the morbidly obese. However, some patients fail to lose any weight after bariatric surgery, and mid-term weight maintenance is variable. The aim of this study was to investigate whether initial WL could predict mid-term weight maintenance. Methods: Eighty patients were enrolled, of whom 44 were treated with the BioEnterics Intragastric Balloon (BIB), 21 with laparoscopic adjustable gastric lap-banding (LAGB), and 15 with laparoscopic sleeve gastrectomy (LSG). Percentage of body WL and percentage of excess weight loss (EWL) were calculated at baseline and after 1, 3, 6, and 12 months. Successful WL was defined as EWL > 20% for patients treated with BIB and > 50% for patients treated with LAGB and SG. Results: Success in the 6th and 12th month was achieved in 80% and 58% of patients in the BIB group, 33% and 40% in the LAGB group, and 60% and 73% in the LSG group. In the BIB group, WL in the 1st month correlated positively with WL at the 6th and 12th month, and an initial WL > 6.5% best predicted success (sensitivity 50%, specificity 80%). A similar association was observed in the LAGB group at the 6th and 12th month and an initial WL > 9.4% best predicted success (sensitivity 90.0%, specificity 81.2%). In patients treated with LSG, WL in the 3rd month correlated positively with EWL at the 6th and 12th month, with a cutoff value of 17% (sensitivity 66.7%, specificity 100%). Conclusions: WL in the 1st month in patients treated with BIB and LAGB and WL in the 3rd month in patients treated with LSG could be used as a prognostic factor to predict mid-term weight maintenance.