| Date | Tournament |
| Sat., Nov. 6, 1999 | Downers Grove North High School (Varsity/Novice-4) |
| Sat., Nov. 13, 1999 | Downers Grove South High School (Novice-2) |
| Sat., Nov. 13, 1999 | Wheaton North High School (2) |
| Sat., Nov. 20, 1999 | (Turkey Tourney) Thornton High School (4) |
| Tues. Nov. 23, 1999 | SICA Novice-- Carl Sandburg High School (2) |
| Fri.-Sat., Dec. 3-4, 1999 | Bradley University (6) |
| Fri., Dec. 10, 1999 | (Santaburg-Oaklaus) Oak Lawn Community High School (All) |
| Sat., Dec. 11, 1999 | (Tree Tourney) Thornridge High School (4) |
| Sat., Jan. 8, 2000 | (Tiger Topper Tourney) Wheaton-Warrenville South High School (4) |
| Sat., Jan. 8, 2000 | Richards High School (Novice-2) |
| Sat., Jan. 15, 2000 | (T-Shirt Tourney) Thornwood High School (4) |
| Fri.-Sat., Jan. 21-22, 2000 | Downers Grove South High School (Varsity-3) |
| Sat., Jan. 22, 2000 | Lincoln-Way High School (Novice-3) |
| Sat., Jan. 29, 2000 | Conference/SICA Varsity-- Shepard High School (2) |
| Sat., Feb. 5, 2000 | Regionals-- Carl Sandburg High School (1) |
| Sat., Feb. 12, 2000 | Sectionals-- Oak Lawn Community High School* |
| Fri.-Sat., Feb. 18-19, 2000 | State-- Elk Grove High School* |
| Apr. 15, 2000 | NFL Districts-- Downers Grove South High School |
