Category | Thursday Sept. 18, 2008 12:45 — 1:45 p.m. Stage 2 | Saturday Sept. 20, 2008 2:15 — 3:15 p.m. Stage 3 |
| Winfield Songs | Winner: Larry Martin Winfield Saturday Night | Winner: Raleigh Hinman Plunder in Winfield |
| Alternate: Joe & DeDe Taverner Don’t It Feed Good to Get Back Home | Alternate: Dave Irwin Thinkin’ About Going to Winfield | |
| Feelin’ Good | Winner: Bryan Masters 2 Flat Top Guitars | Winner: Tedi Jean May Lucky List |
| Alternate: Shawn Cole Bonfire | Alternate: Jill Hobbs Berry Pickin’ | |
| Children | Winner: Rick Malsick Christmas Tumbleweed | Winner: Tony Wentersdorf Pluto |
| Alternate: Larry Taverner Dumm Dada Da | Alternate: David Hall Birthday Suit | |
| Love Songs | Winner: Kenny Cornell He’ll Always Be My Baby | Winner: Helen Avakian I Love the Moon |
| Alternate: Rick Malsick Bestest Love | Alternate: Jimmy DeHeno I Think She Likes Me | |
| Better World | Winner: Lori Holyfield Pay Attention | Winner: Paul Whiteley Your Heart is a Muscle the Size of Your Fist |
| Alternate: Mark Horton Seed by Seed | Alternate: Quentin Stephens The Pathway | |
| Feelin’ Blue | Winner: Jimmy DeHeno Cheap Guitars | Winner: Mary Henderson Bittersweet & Blue |
| Alternate: Bryan & Bernice Hembree Coalmine Moonshine | Alternate: Larry Martin Starting Over | |
| Humorous | Winner: Dan O’Brien Worn Out Strings | Winner: Lou-Lou Barbour Don Green’s Hog Liquor |
| Alternate: Kenny Cornell A Girl Like Me | Alternate: Harry Hewlett Road Kill of Love | |
| Religion/Spirit | Winner: Mark Merryman Wooden Cross | Winner: Bayard Blaine / Bryan Hembree Dig a Little Deeper |
| Alternate: Rick Malsick Joseph’s Song | Alternate: Kara Barnard Final Trail | |
| Instrumental | Winner: Gary Mortensen Haunted Saddle | Winner: Quentin Stephens Avatar |
| Alternate: Mike & Dayle Black Dan Kessinger’s | Alternate: Kim McKee Kiota Bell | |
| None of the Above | Winner: Robert Runyon & Gerald G. Lucas Elvis Johnson | Winner: Shannon Wurst Concrete and Clay |
| Alternate: S.L.Reay & Ernie Martinez One Lonely Rider | Alternate: David Dearnley Jenny Lyn |
