Sport leadership research continues to focus on the study of selected situational variables and their relationship to leadership effectiveness. Blanchard's Situational Leadership II Theory (Blanchard, 1985) is a popular leaderhip theory that has practical appeal but very little research support in the literature. The theory emphasizes the importance of matching leadership style with the maturity/development levels of followers or subordinates in order to optimize leadership effectiveness. When an athlete (or group of athletes) is at the M1 or D1 maturity/development level, the theory indicates that a S1 (high task/low relationship) style would be the best leadership style to use with this athlete or group of athletes. If the athlete is functioning at the M2/D2 level,then an S2 (high task/high relationship) style would be most effective, etc. The purpose of this study was to test basic tenets of the Situational Leadership II Theory in a sport setting by examining individual as well as group scores. It was hypothized that when a "match" occurred between the leadership style of the coach and the maturity/development level of an individual athlete or a group of athletes, then performance would be at the highest levels. Nine special position coaches and fifty-four players on an NCAA Division I football team participated in this study. The special position coaches completed a performance rating scale for each player in their special position units at the beginning and end of spring football. The coaches also completed a maturity/ development level scale for each athlete and, in turn, the players completed the Leadership Scale for Sport (LSS) (Chelladurai & Saleh, 1980) on their special position coach. Group and individual scores were calculated. A variety of statistical tests were run to determine if statistical differences existed between the groups on selected variables. No statistically significant differences were found but a number of interesting trends were identified. Keyword(s): administration/mgmt, leadership development, sport management