Background: Diabetic foot is one of the most prevalent complications of diabetes. It has the potential risk of pathologic consequences including infection, ulceration and amputation, and is associated with disability, death and substantial costs. Diabetic foot result from neuropathy and/or ischemia and the premature identification of risk factors may avoid ulcerations and amputations. Several benefits in this area can be induced by different exercise programs, although effects of physical activity have a dose–response pattern. Aim: This study aimed to investigate the association between foot ulceration risk and adherence to a multi-component exercise program in middle-aged and older patients with type 2 diabetes (T2D). Method: The study involved 79 individuals with T2D recruited from primary health care units to participate in Diabetes em Movimento® Vila Real (Portugal). This community-based exercise program is composed by three exercise sessions per week, 75 min per session (aerobic, resistance, agility/balance, and stretching exercise), during nine months. Risk of ulceration was assessed before and after the exercise program, with a protocol that included patients’ relevant clinical history, clinical foot examination (observation of structural and dermatological characteristics, 10-g Semmes-Weinstein monofilament test, 128-Hz tuning fork test, and palpation of peripheral arterial pulses), and the evaluation of the difficulties in taking care of the feet (ability to see both the plantar surfaces). One-way ANOVA was used to analyze the association between exercise program adherence and changes in the risk of ulceration (improved, unchanged, worsened). Results: 75 individuals concluded the study and were included in final analysis (35 men, 40 women 64.43 ± 7.05 years old, body mass index 29.98 ± 4.41 kg/m2, non-smokers). After nine months of exercise (overall exercise intensity of 12.73 ± 0.95 points in Borg rating of perceived exertion scale of 6–20 points), 26 subjects (34.7%) decreased risk of ulceration, 35 (46.7%) maintained the risk, and 14 (18.6%) increased the risk. Those who decreased the risk had higher adherence to exercise program than those who increased the risk (65.60% versus 45.43%, p < 0.05, partial η2 = 0.14). Overall, participants’ adherence to exercise was 58.85 ± 25.18 % (ranging from 3.70 to 98.15%). Discussion: The results of this study suggest that higher compliance to an exercise program seems associated with a decrease in the risk of foot ulceration in middle-aged and older patients with T2D. Besides the need for implementation exercise programs for T2D control and related comorbidities, there is an urgent demand to develop motivation strategies to increase exercise adherence in order to maximize physical activity benefits. Funding: This work was supported by the Foundation for Science and Technology (FCT, Portugal) and European Social Fund (ESF), through a Doctoral grant endorsed to the first author (SFRH/BD/143195/2019) under the Norte 2020 – Norte’s Regional Operation Programme.