(1) Background: Male stress incontinence in patients with previously treated urethral or bladder neck stricture is a therapeutic challenge. The efficacy and safety of the adjustable trans-obturator male system (ATOMS) in these patients is unknown. (2) Methods: All patients with primary ATOMS implants in our institution between 2014 and 2021 were included. The outcomes of patients with previously treated urethral or bladder neck stricture (≥6 months before ATOMS implant) and stable 16Ch urethral caliber were compared to those without a history of stricture. The primary endpoint was the dry patient rate, defined as the pad test ≤ 20 mL/day, and complication rate, including device removal. The secondary variable was self-perceived satisfaction using the Patient Global Impression of Improvement (PGI-I) scale. Wilcoxon rank sum test, Fisher’s exact test and logistic regression were performed. (3) Results: One hundred and forty-nine consecutive patients were included, twenty-one (14%) previously treated for urethral or bladder neck stricture (seven urethroplasty, nine internal urethrotomy and five bladder neck incision). After ATOMS adjustment, 38% of the patients with treated stricture were continent compared to 83% of those without (p < 0.0001). After weighted matched observations using propensity score pairing, the proportion of continent patients without a previous stricture was 56% (p = 0.236). Complications occurred in 29% of the patients with stricture and in 20% of those without (p = 0.34). The severity of the complications was distributed evenly among the groups (p = 0.42). Regarding self-perceived satisfaction with the implant, 90% of the patients with stricture perceived the results satisfactorily (PGI-I 1–3) compared to 97% of the rest (p = 0.167). Stricture was associated with radiotherapy (p < 0.0001) and time from prostatectomy to implantation (p = 0.012). There was a moderate correlation between previous stricture and the severity of incontinence, both evaluated according to the 24-h pad test (Rho = 0.378; p < 0.0001) and the ICIQ-SF questionnaire (Rho = 0.351; p < 0.0001). Multivariate analysis for the factors predictive of failure after ATOMS adjustment revealed previous stricture (OR 4.66; 95% CI 1.2–18.87), baseline 24-h pad test (per 100 mL, OR 1.28; 95% CI 1.09–1.52) and final cushion volume (per mL, OR 1.34; 95% CI 1.19–1.55). This model predicted dryness with an AUC of 92%. After the PSMATCH procedure using a propensity score, the model remained unchanged, with the previous stricture (OR 8.05; 95% CI 1.08–110.83), baseline 24-h pad test (per 100 mL, OR 1.53; 95% CI 1.15–2.26) and final cushion volume (per mL, OR 1.45; 95% CI 1.17–2) being independent predictors and an AUC of 93%. (4) Conclusions: ATOMS can be used to treat male stress incontinence in patients with a history of stricture, although the effectiveness of the device is reduced. On the other hand, the security and perceived satisfaction were equivalent for both groups.