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(1) Background: High bleeding risk is associated with adverse outcomes in ACS patients. We aimed to evaluate temporal trends in treatment and outcomes of ACS patients according to bleeding risk. (2) Methods: Included were ACS patients enrolled in ACSIS surveys. Patients were divided into three groups according to enrolment period: early (2002–2004), mid (2006–2010) and recent (2012–2018). Each group was further stratified into three subgroups according to CRUSADE bleeding risk score. The primary endpoints were 30-day MACE and 1-year all-cause mortality. (3) Results: Included were 13,058 ACS patients. High bleeding risk patients were less frequently treated with guideline-based medications and coronary revascularization. They also had higher rates of 30-day MACE and 1-year all-cause mortality regardless of the enrollment period. Among patients enrolled in early period, 30-day MACE rates were 10.8%, 17.5% and 24.3% (<i>p</i> < 0.001) and 1-year all-cause mortality rates were 2%, 7.7% and 23.6% (<i>p</i> < 0.001) in the low, moderate and high bleeding risk groups, respectively. Among patients enrolled in mid period, 30-day MACE rates were 7.7%, 13.4% and 23.5% (<i>p</i> < 0.001) and 1-year all-cause mortality rates were 1.5%, 7.2% and 22.1% (<i>p</i> < 0.001) in low, moderate and high bleeding risk groups, respectively. For patients enrolled in recent period, 30-day MACE rates were 5.7%, 8.6% and 16.2%, (<i>p</i> < 0.001) and 1-year all-cause mortality rates were 2.1%, 6% and 22.4%, (<i>p</i> < 0.001) in low, moderate and high bleeding risk groups, respectively. These differences remained significant following a multivariate analysis. (4) Conclusions: The percentage of patients at high bleeding risk has decreased over the last years. Despite recent improvements in the treatment of ACS patients, high bleeding risk remains a strong predictor of adverse outcomes.