The National Hockey League (NHL) is one of the four major sports in North America. Following the lockout of 2004-2005, the league felt it was necessary to introduce a team salary cap which prevents teams from spending a certain dollar amount on player salaries. As a young player enters free agency, general managers must negotiate an efficient contract which keeps the team under the salary cap in addition to paying the player the necessary money for his talent. The purpose of this study is to analyze NHL player's first and second year productiveness to find the true worth of these players as they enter free agency and long-term contracts. To accomplish this, results were found using Ordinary Least Squares (OLS) and Fixed Effects Models regression along with the collection of players' first and second year NHL season between 2005 and 2009. Furthermore, this thesis believes that NHL players increase productivity from their first to second year. If young NHL players do increase their production from season to season, it may prove beneficial to teams and general managers as they will be able to build a cost-efficient team due to contracts that are suitable to each player's ability.