Background: This study aimed to investigate the influence of the dietary approaches to stop hypertension (DASH) diet on gestational weight gain and perinatal outcomes in pregnant women with pre-existing diabetes mellitus (PDM). Methods: A randomized, single-blind, controlled clinical trial was conducted with 68 pregnant women with PDM throughout prenatal care until delivery (18 weeks) at a public maternity hospital in Rio de Janeiro, Brazil (2016–2020). The standard diet adopted by the control group (standard diet group—SDG) contained 45–55% carbohydrates, 15–20% protein, and 25–30% lipids of the total energy intake. An adapted DASH diet, with a similar macronutrient composition, but with higher calcium, potassium, magnesium, fiber, and reduced saturated fat, was prescribed for the intervention group (DASH diet group—DDG). Student’s t- or Mann–Whitney U tests were used to compare outcomes between groups. To assess the trajectory of gestational weight gain throughout the intervention between the study groups, linear mixed-effects regression models were used. Results: The DDG had lower gestational weight gain at the fifth (p = 0.03) and seventh appointment (p = 0.04), with no difference in average total gestational weight gain (SDG: 10 kg [SD = 4]; DDG: 9 kg [SD = 5], p = 0.23). There was a trend for a lower length of stay of the newborns (p = 0.08) in the DDG without differences for other perinatal outcomes. Conclusions: The DASH diet promoted less variation in gestational weight gain without promoting a difference in total gestational weight gain, and there was no difference between the study groups for perinatal outcomes.