Using a matched sampling method, this research examined the process of sex-based differentiation in sentencing outcomes for 194 men and 194 women, sentenced over a seven-year period in Christchurch, New Zealand. Consistent with past research, our results showed that judicial processing treated women more leniently than men. Path analyses revealed that judges were less likely to sentence women than men to imprisonment terms because of gendered information and decisions made earlier in the judicial process, such as criminal history, length of custodial remands, and pre-sentence recommendations by probation officers. In contrast, judges exercised considerable leniency towards women (compared with men) in setting the length of prison terms, even after statistically controlling for all sex-differentiated factors such as criminal history. Explanations and implications are discussed.