(1) Background: COVID-19 virtual learning reduced structural supports for adolescent physical activity and diet, threatening metabolic health, especially in teens with overweight or obesity (OWOB). (2) Methods: Adolescents (N = 14) with OWOB completed fasting blood draws (measuring insulin resistance, IR) and Dual Energy X-Ray Absorptiometry (DXA, measuring total body fat percent, TBF%) pre-COVID-19 and during COVID-19. Changes in TBF% and IR were calculated (1) pre-COVID-19 and (2) from pre-COVID-19 to during COVID-19. Age and body mass index (BMI) percentile-matched data assessed normative changes across similar, non-COVID-19 time periods. Paired t-tests compared TBF% change pre- to during COVID-19 with (1) TBF% change pre-COVID19 and (2) TBF% normative change. Two ANCOVAs compared IR change pre- to during COVID-19 with (1) IR change pre-COVID-19 controlling for BMI z-score and difference in time between assessments and (2) normative change in IR controlling for sex/race. (3) Results: The TBF% change pre-COVID-19 and the normative change were similar. The TBF% increased more (~six percentage points) during COVID-19 compared to normative change (p < 0.01). During COVID-19, IR increased more (~2.5 units) than change pre-COVID-19 (p = 0.03) and increased more (~3.5 units) than normative change (p = 0.01). (4) Conclusions: TBF% and IR increased exponentially during COVID-19 in teens with OWOB compared to pre-COVID-19 and normative changes.