Points for the NACDA Directors' Cup are based on order of finish in various championships sponsored by the National Collegiate Athletic Association (NCAA) and the National Association of Intercollegiate Athletics (NAIA) or, in the case of Division I Football, media-based polls.

In Division II, UC Davis won six of the first eight awards, but its athletic program moved to Division I in 2003 and Grand Valley State has won 16 of the 19 awards since as of 2024 (the title went unawarded for two years due to COVID-19).

The only other current Division II member with an award is 1999 winner Adams State.

SFU left U Sports in 2011 and has since become a full member of NCAA Division II.

From 2004–05 to 2011–12, Azusa Pacific University assumed the mantle at the NAIA level, winning eight consecutive championships before moving to NCAA Division II in the 2012–13 season.

Oklahoma City University has been the most successful school since that year, with three Directors' Cups in the 2010s and four overall.

The scoring structure has been criticized for several reasons, especially due to the number of sports counted per division.

This gives Stanford more opportunities to win titles than most other schools, especially considering that some of the sports Stanford sponsors are not played by very many other schools (5 out of 31 have championship fields under 20 teams, and one [namely men's gymnastics] has fewer than 20 sponsoring schools), all but guaranteeing a substantial number of points for the few schools that do (NACDA awards significantly fewer points for teams that finish lower than fourth in sports with less competition, but the top four teams (except in 8-team and 4-team bracket sports) always receive 100, 90, 85, and 80 points respectively).