Given the increased risk factors in the transition from middle school to high school, this study tracked academic and school discipline records for students receiving general and special education services as they transitioned from Grade 8 to Grade 9. The authors employed analysis of variance and structural equation modeling to determine the significance and strength of the relationship between academic skills and behavior variables. Results indicated significant interactions between academic scores and office discipline referrals, both within and across grades. When controlling for the direct effects, crossover effects of Grade 8 discipline referrals on Grade 9 academic scores remained statistically significant, though effects of Grade 8 state reading assessment scores on Grade 9 discipline referrals did not. Results are discussed in terms of improving school environments and academic instruction to prevent school failure. (Contains 4 figures and 3 tables.)