Background: The Pitch Smart guidelines aim to limit youth baseball pitching behaviors associated with overuse injuries. Despite many youth baseball leagues being compliant with the guidelines, during tournaments, pitch count restrictions or guidelines are often not followed. Purpose: To perform a quantitative analysis of pitch counts in youth baseball players and evaluate compliance with regard to the Pitch Smart guidelines in the tournament setting. Study Design: Cross-sectional study; Level of evidence, 3. Methods: Included in the analysis were 100 youth baseball teams that competed in the 8-and-under to 14-and-under age divisions during the 2019 tournament season. Pitching data were compared with the Pitch Smart guidelines. Violations were identified as (1) exceeding maximum daily pitch count, (2) inadequate rest between pitching events, and (3) pitching more than 1 event on the same day. Pitcher and game factors were analyzed for possible relationships to guideline violations using mixed-effects negative binomial regression models, with comparisons of violations using rate ratios (RRs). Results: Analysis included 1046 pitchers and 2439 games. There were 1866 total Pitch Smart guideline violations, with 48.6% of pitchers having at least 1 violation. Inadequate rest was the most common reason for violation, with noncompliance occurring in 43.3% of pitchers. The highest rate of any violation (0.32 per appearance) occurred in the 8-and-under age division. High-volume pitchers had increased violation rates in each category compared with low-volume pitchers ( P < .001). Violation rates were increased more than twice the rate when pitchers participated in ≥5 consecutive games without a rest day when compared with a single game (RR, 2.48; P < .001). Conclusion: Noncompliance with Pitch Smart guidelines in tournament settings occurred in more than 90% of teams and almost half of all pitchers. Factors associated with noncompliance included younger pitcher age, high-volume pitching, and pitching in multiple consecutive games. Education of tournament directors, coaches, parents, and athletes regarding pitching guidelines is warranted in order to limit the risk of injury.