The need to develop household personal finance literacy is an increasingly important issue in many countries, especially in the wake of the latest financial crisis. The literature broadly demonstrates that most individuals do not have an adequate level of financial literacy. A number of initiatives aimed at different groups (usually defined by gender, age, work status and income) have been developed. The present paper is part of a strand of literature that focuses on the financial literacy of university students, and in particular, the potential benefits of their participation in investment simulations, in terms of improved skills and knowledge. It analyzes an innovative online portfolio management competition for graduate students, the Fund Management Challenge, which is promoted by the CFA Society Italy. The results demonstrate how this Challenge, and investment simulations in general, set with specific rules to mitigate opportunistic behaviors, can help to improve participants' financial literacy levels. In addition to this, the use of quality indicators encourages students to learn and helps mentors and educators to better allocate resources to those in need of assistance. The study represents an original analysis of the Challenge. If further analysis supports this preliminary evidence, the Challenge could become a reference point for future investment simulations targeting university students.