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Country Radio Top 20 | |||
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12/10/1999 | |||
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| 1 | 2 | When I Said I Do Clint Black w/ Lisa Hartman-Black | 11 |
| 2 | 1 | He Didn't Have To Be Brad Paisley | 10 |
| 3 | 3 | Breathe Faith Hill | 7 |
| 4 | 4 | Home To You John Michael Montgomery | 13 |
| 5 | 7 | What Do You Say Reba McEntire | 8 |
| 6 | 5 | I Love You Martina McBride | 18 |
| 7 | 9 | Pop A Top Alan Jackson | 6 |
| 8 | 8 | All Things Considered Yankee Grey | 9 |
| 9 | 12 | Cowboy Take Me Away Dixie Chicks | 4 |
| 10 | 6 | Come On Over Shania Twain | 10 |
| 11 | 13 | My Best Friend Tim McGraw | 4 |
| 12 | 11 | Big Deal LeAnn Rimes | 6 |
| 13 | 10 | Something Like That Tim McGraw | 19 |
| 14 | 15 | She Thinks My Tractor's Sexy Kenny Chesney | 5 |
| 15 | 16 | Smile Lonestar | 2 |
| 16 | 14 | What Do You Say To That George Strait | 16 |
| 17 | 17 | Live, Laugh, Love Clay Walker | 3 |
| 18 | 18 | Steam Ty Herndon | 3 |
| 19 | 20 | Put Your Hand In Mine Tracy Byrd | 2 |
| 20 | 19 | Amazed Lonestar | 29 |