| Sectional 1
 @ Woodridge Jefferson | 
| Host: Woodridge Jefferson Date: Wednesday, February 12, 2014
 | 
| Bellwood Roosevelt
 (12-1)
 vs. 
Rockford Flinn
 (16-6) | 
| Regional 1 | Bellwood Roosevelt
 def. Bolingbrook Jane Addams
, 63-45 | 
| Regional 2 | Rockford Flinn
 def. Rockford West
, 60-47 | 
| Sectional 2
 @ FOREST TRAIL | 
| Host: Park Forest Forest Trail Date: Wednesday, February 12, 2014
 | 
| Phoenix Coolidge
 (16-2)
 vs. 
Park Forest Forest Trail
 (21-1) | 
| Regional 3 | Phoenix Coolidge
 def. Calumet City Dirksen
, 55-24 | 
| Regional 4 | Park Forest Forest Trail
 def. Flossmoor Parker
, 78-44 | 
| Sectional 3
 @ Frankfort Summit Hill | 
| Host: Frankfort Summit Hill Date: Wednesday, February 12, 2014
 | 
| Frankfort Hickory Creek
 (22-1)
 vs. 
Matteson Colin Powell
 (19-2) | 
| Regional 5 | Frankfort Hickory Creek
 def. Frankfort Summit Hill
, 44-21 | 
| Regional 6 | Matteson Colin Powell
 def. Bourbonnais UGC
, 53-32 | 
| Sectional 4
 @ Minooka Junior High School | 
| Host: Minooka Date: Wednesday, February 12, 2014
 | 
| Joliet Dirksen
 (13-6)
 vs. 
Forrest Prairie Central
 (19-5) | 
| Regional 7 | Joliet Dirksen
 def. Shorewood Troy
, 55-37 | 
| Regional 8 | Forrest Prairie Central
 def. Channahon
, 39-38 | 
| Sectional 5
 @ Morton JHS | 
| Host: Morton JHS Date: Wednesday, February 12, 2014
 | 
| Normal Chiddix
 (17-5)
 vs. 
Pekin Broadmoor
 (19-4) | 
| Regional 9 | Normal Chiddix
 def. Bloomington JHS
, 33-31 | 
| Regional 10 | Pekin Broadmoor
 def. Morton JHS
, 46-25 | 
| Sectional 6
 @ Rocket Center | 
| Host: Tolono Unity Date: Wednesday, February 12, 2014
 | 
| Danville North Ridge
 (14-3)
 vs. 
Effingham JHS
 (16-2) | 
| Regional 11 | Danville North Ridge
 def. Champaign Franklin
, 38-37 | 
| Regional 12 | Effingham JHS
 def. Champaign Edison
, 46-43 | 
| Sectional 7
 @ Taylorville Junior High School | 
| Host: Taylorville JHS Date: Wednesday, February 12, 2014
 | 
| Mt. Zion
 (17-5)
 vs. 
Quincy
 (11-7) | 
| Regional 13 | Mt. Zion
 def. Decatur Stephen Decatur
, 44-27 | 
| Regional 14 | Quincy
 def. Springfield Jefferson
, 71-50 | 
| Sectional 8
 @ East St. Louis Lincoln Middle School | 
| Host: East St. Louis Lincoln Date: Wednesday, February 12, 2014
 | 
| East St. Louis Lincoln
 (20-3)
 vs. 
Alton
 (15-9) | 
| Regional 15 | East St. Louis Lincoln
 def. Cahokia Wirth
, 43-32 | 
| Regional 16 | Alton
 def. Bethalto Trimpe
, 53-34 |