| 1999 Challenge Cup-- October 30 & 31 at Tompkinsville | |||
| Saturday - Alternate Shot (9 Holes) | |||
| Rodney Biggerstaff & Lowery Anderson | Hidden Hills 2 & 1 | Mark Shipley & Darren Shirley | |
| David Anderson & Michael Carter | Johnny Belcher & Freddie Vandeveer | Glasgow 2 & 1 | |
| Benny Simpson & Trevor Glass | Bobby McDaniel & Phillip Bale | Glasgow 3 & 2 | |
| Jonathon Shaw & Scott Rush | Spencer Botts & Stacy Sutherland | Glasgow 2 & 1 | |
| Stevie Guffey & Bud Hoffman | Hidden Hills 1 Up | Jim Berry & Bernard Lawerence | |
| Neal Isenberg & Johnny Paul Nixon | Bryan Baysinger & Sam Dickinson | Glasgow 1 Up | |
| Saturday - Fourball | |||
| Stevie Guffey & Bud Hoffman | Bernard Lawerence & Mark Shipley | Glasgow 1 Up | |
| Neal Isenberg & Trevor Glass | Hidden Hills 3 & 2 | Darren Shirley & Sam Dickinson | |
| Michael Carter & Jonathon Shaw | Hidden Hills 3 & 2 | Jim Berry & Spencer Botts | |
| Rodney Biggerstaff & Lowery Anderson | Johnny Belcher & Bobby McDaniel | Glasgow 2 & 1 | |
| Johnny Paul Nixon & Benny Simpson | Hidden Hills 1 Up | Freddie Vandeveer & Phillip Bale | |
| Scott Rush & David Anderson | Bryan Baysinger & Stacy Sutherland | Glasgow 5 & 4 | |
| Sunday - Individual | |||
| Bud Hoffman | Stacy Sutherland | Glasgow 1 Up | |
| David Anderson | Jim Berry | Glasgow 2 & 1 | |
| Jonathon Shaw | Hidden Hills 6 & 5 | Spencer Botts | |
| Trevor Glass | Bobby McDaniel | Glasgow 1 Up | |
| Scott Rush | Sam Dickinson | Glasgow 2 & 1 | |
| Benny Simpson | Hidden Hills 4 & 2 | Phillip Bale | |
| Stevie Guffey | Hidden Hills 5 & 4 | Bernard Lawerence | |
| Neal Isenberg | Hidden Hills 1 Up | Mark Shipley | |
| Johnny Paul Nixon | Darren Shirley | Glasgow 6 & 5 | |
| Lowery Anderson | Freddie Vandeveer | Glasgow 3 & 2 | |
| Rodney Biggerstaff | Hidden Hills 2 & 1 | Johnny Belcher | |
| Michael Carter | Bryan Baysinger | Glasgow 2 & 1 | |
| Hidden Hills | Glasgow | ||
| 10 | 14 | ||