The Ultimate Challenge was developed in 1990 as an opportunity for a creative way for students and faculty to interact, compete, foster friendship and build community. The friendly competition between business faculty and students have through the years seen faculty face off with students in sand volleyball, bowling, golf, softball, HORSE, investment challenge, table games i.e. Trivial Pursuit, tennis, and croquet to name a few. The quest each year is for the mythical title, known as the Gresham Cup (named for the university president, Dr. Loren Gresham).

The Gresham Cup
The scorecard for the history of the Ultimate Challenge is as follows:
| 1990-1991 |
Faculty- 297 |
Students-243 |
| 1991-1992 |
Faculty-149 |
Students-139 |
| 1992-1993 |
Faculty-172 |
Students-128 |
| 1993-1994 |
Faculty-134 |
Students-126 |
| 1994-1995 |
Faculty-165 |
Students-113 |
| 1995-1996 |
Faculty-131 |
Students-130 |
| 1996-1997 |
Faculty-120 |
Students-80 |
| 1997-1998 |
Faculty-200 |
Students-0 |
| 1998-1999 |
Faculty-120 |
Students-80 |
| 1999-2000 |
Faculty-0 |
Students-160 |
| 2000-2001 |
Faculty-80 |
Students-60 |
| 2001-2002 |
Faculty-60 |
Students- 120 |
| 2002-2003 |
Faculty-50 |
Students-0 |