| Pleasant Plains | 1999-2000 | Boys' Baseball | A |
| Winnetka (New Trier) | 1999-2000 | Boys' Baseball | AA |
| Pleasant Plains | 1999-2000 | Boys' Basketball | A |
| Aurora (West Aurora) | 1999-2000 | Boys' Basketball | AA |
| Eureka | 1999-2000 | Boys' Cross Country | A |
| Elmhurst (York) | 1999-2000 | Boys' Cross Country | AA |
| Carthage | 1999-2000 | Boys' Football | 1A |
| Stillman Valley | 1999-2000 | Boys' Football | 2A |
| Byron | 1999-2000 | Boys' Football | 3A |
| Joliet (Catholic Academy) | 1999-2000 | Boys' Football | 4A |
| Chicago (Mt. Carmel) | 1999-2000 | Boys' Football | 5A |
| Naperville (Central) | 1999-2000 | Boys' Football | 6A |
| Rochester | 1999-2000 | Boys' Golf | A |
| Fairbury (Prairie Central) | 1999-2000 | Boys' Golf | A |
| Lake Forest (H.S.) | 1999-2000 | Boys' Golf | AA |
| Mundelein (H.S.) | 1999-2000 | Boys' Gymnastics | — |
| Crystal Lake (Prairie Ridge) | 1999-2000 | Boys' Soccer | A |
| East Moline (United) | 1999-2000 | Boys' Soccer | AA |
| Aurora (Marmion Academy) | 1999-2000 | Boys' Swimming and Diving | — |
| Winnetka (New Trier) | 1999-2000 | Boys' Tennis | — |
| St. Joseph (S.J.-Ogden) | 1999-2000 | Boys' Track and Field | A |
| Elmhurst (York) | 1999-2000 | Boys' Track and Field | AA |
| Orland Park (Sandburg) | 1999-2000 | Boys' Volleyball | — |
| Lombard (Montini) | 1999-2000 | Boys' Wrestling | A |
| New Lenox (Providence Catholic) | 1999-2000 | Boys' Wrestling | AA |
| Evanston (Twp.) | 1999-2000 | Chess | — |
| Flossmoor (Homewood-F.) | 1999-2000 | Drama and Group Interpretation | — |
| Tinley Park (Andrew) | 1999-2000 | Girls' Badminton | — |
| Okawville | 1999-2000 | Girls' Basketball | A |
| Buffalo Grove | 1999-2000 | Girls' Basketball | AA |
| Machesney Park (Harlem) | 1999-2000 | Girls' Bowling | — |
| Winnebago | 1999-2000 | Girls' Cross Country | A |
| Schaumburg (H.S.) | 1999-2000 | Girls' Cross Country | AA |
| St. Charles (H.S.) | 1999-2000 | Girls' Golf | — |
| Barrington | 1999-2000 | Girls' Gymnastics | — |
| St. Charles (H.S.) | 1999-2000 | Girls' Soccer | — |
| Casey (C.-Westfield) | 1999-2000 | Girls' Softball | A |
| Joliet (Twp.) | 1999-2000 | Girls' Softball | AA |
| St. Charles (H.S.) | 1999-2000 | Girls' Swimming and Diving | — |
| Hinsdale (Central) | 1999-2000 | Girls' Tennis | — |
| St. Joseph (S.J.-Ogden) | 1999-2000 | Girls' Track and Field | A |
| Chicago (Morgan Park) | 1999-2000 | Girls' Track and Field | AA |
| Normal (University) | 1999-2000 | Girls' Volleyball | A |
| Downers Grove (South) | 1999-2000 | Girls' Volleyball | AA |
| Ottawa (Twp.) | 1999-2000 | Music Sweepstakes | A |
| Moline (H.S.) | 1999-2000 | Music Sweepstakes | AA |
| Herscher | 1999-2000 | Music Sweepstakes | B |
| Forreston | 1999-2000 | Music Sweepstakes | C |
| Ashland (A-C Central) | 1999-2000 | Music Sweepstakes | D |
| Byron | 1999-2000 | Scholastic Bowl | A |
| Lincolnshire (Stevenson) | 1999-2000 | Scholastic Bowl | AA |
| Wheaton (W. Warrenville South) | 1999-2000 | Speech Individual Events | — |
