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<b><i>Introduction:</i></b> Endoscopic retrograde cholangiopancreatography (ERCP) in patients with Billroth II gastrectomy is still a challenging procedure. The optimal approach, namely the type of endoscope and sphincter management, has yet to be defined. <b><i>Aim:</i></b> To compare the efficacy and safety of forward-viewing gastroscope and the side-viewing duodenoscope in ERCP of patients with Billroth II gastrectomy. <b><i>Methods:</i></b> We conducted a retrospective, single-center cohort study of consecutive patients with Billroth II gastrectomy submitted to ERCP in an expert center for ERCP between 2005 and 2021. The outcomes assessed were: papilla identification, deep biliary cannulation, and adverse events (AEs). Multivariate analysis was performed to evaluate potential associations and predictors of the main outcomes. <b><i>Results:</i></b> We included 83 patients with a median age of 73 (IQR 65–81) years. ERCP was performed using side-viewing duodenoscope in 52 and forward-viewing gastroscope in 31 patients. Patients’ characteristics were similar in the two groups. The global rate of papilla identification was 66% (<i>n</i> = 55). The rate of deep cannulation was 58% considering all patients and 87% in the subgroup of patients in which the papilla major was identified. Cannulation was performed with standard methods in 65% of cases and with needle-knife fistulotomy in 35%. AEs occurred in 4 patients. There was no difference between duodenoscope and gastroscope in papilla identification (64% [95% CI: 51–77] vs. 71% [55–87]). Although not statistically significant, duodenoscope had a lower deep cannulation rate when considering all patients (52% [15–39] vs. 68% [7–35]) and a higher AEs rate (8% [1–15] vs. 0% [0–1]). In a multivariate analysis, the use of gastroscope significantly increased the deep cannulation rate (OR = 152.62 [2.5–9,283.6]). <b><i>Conclusion:</i></b> This study demonstrates that forward-viewing gastroscope is at least as effective and safe as side-viewing duodenoscope for ERCP in patients with Billroth II gastrectomy. Moreover, our study showed that gastroscope is an independent predictor of successful cannulation.