Numerous approaches to student modeling have been proposed since the inception of the field more than three decades ago. hat the field is lacking completely is comparative analyses of different student modeling approaches. Such analyses are sorely needed, as they can identify the most promising approaches and provide guidelines for future research. In this paper we compare Cognitive Tutoring to Constraint-Based Modeling (CBM). We present our experiences in implementing a database design tutor using both methodologies and highlight their strengths and weaknesses. We compare their characteristics and argue the differences are often more apparent than real. For specific domains, one approach may be favoured over the other, making them viable complementary methods for supporting learning.