| Sectional 1
 @ Jefferson Jr. High | 
| Host: Woodridge Jefferson Date: Wednesday, February 05, 2014
 | 
| Bolingbrook Brooks
 (19-0)
 vs. 
Rockford Lincoln
 (17-1) | 
| Regional 1 | Bolingbrook Brooks
 def. Woodridge Jefferson
, 34-32 | 
| Regional 2 | Rockford Lincoln
 def. Rockford Eisenhower
, 35-27 | 
| Sectional 2
 @ FOREST TRAIL | 
| Host: Park Forest Forest Trail Date: Wednesday, February 05, 2014
 | 
| Phoenix Coolidge
 (14-1)
 vs. 
Park Forest Forest Trail
 (15-4) | 
| Regional 3 | Phoenix Coolidge
 def. Sauk Village Rickover
, 52-26 | 
| Regional 4 | Park Forest Forest Trail
 def. University Park Crete Monee
, 40-29 | 
| Sectional 3
 @ Homer Junior High | 
| Host: Homer Glen Homer Date: Wednesday, February 05, 2014
 | 
| Frankfort Hickory Creek
 (18-7)
 vs. 
Matteson Colin Powell
 (18-1) | 
| Regional 5 | Frankfort Hickory Creek
 def. New Lenox Martino
, 37-36 | 
| Regional 6 | Matteson Colin Powell
 def. Peotone
, 44-25 | 
| Sectional 4
 @ Joliet Washington | 
| Host: Joliet Washington Date: Wednesday, February 05, 2014
 | 
| Joliet Hufford
 (20-2)
 vs. 
Minooka
 (14-10) | 
| Regional 7 | Joliet Hufford
 def. Romeoville Lukancic
, 48-38 | 
| Regional 8 | Minooka
 def. Forrest Prairie Central
, 38-25 | 
| Sectional 5
 @ Bloomington Junior High School | 
| Host: Bloomington JHS Date: Thursday, February 06, 2014
 | 
| Normal Parkside
 (21-0)
 vs. 
Morton JHS
 (21-1) | 
| Regional 9 | Normal Parkside
 def. Bloomington JHS
, 40-37 | 
| Regional 10 | Morton JHS
 def. Canton Ingersoll
, 58-24 | 
| Sectional 6
 @ Effingham JHS | 
| Host: Effingham JHS Date: Thursday, February 06, 2014
 | 
| Champaign Franklin
 (21-1)
 vs. 
Effingham JHS
 (16-2) | 
| Regional 11 | Champaign Franklin
 def. Rantoul Eater
, 47-33 | 
| Regional 12 | Effingham JHS
 def. Mattoon
, 44-29 | 
| Sectional 7
 @ Taylorville Junior High School | 
| Host: Taylorville JHS Date: Wednesday, February 05, 2014
 | 
| Taylorville JHS
 (22-0)
 vs. 
Springfield Washington
 (17-4) | 
| Regional 13 | Taylorville JHS
 def. Rochester
, 42-33 | 
| Regional 14 | Springfield Washington
 def. Springfield Jefferson
, 35-31 | 
| Sectional 8
 @ East St. Louis Lincoln Middle School | 
| Host: East St. Louis Lincoln Date: Thursday, February 06, 2014
 | 
| Cahokia Wirth
 (20-0)
 vs. 
Alton
 (14-5) | 
| Regional 15 | Cahokia Wirth
 def. Edwardsville Liberty
, 52-34 | 
| Regional 16 | Alton
 def. Bethalto Trimpe
, 45-28 |