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Country Radio Top 20 | |||
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10/1/1999 | |||
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| 1 | 1 | Something Like That Tim McGraw | 9 |
| 2 | 4 | I Love You Martina McBride | 8 |
| 3 | 2 | Ready To Run Dixie Chicks | 11 |
| 4 | 3 | You Had Me From Hello Kenny Chesney | 14 |
| 5 | 5 | Little Man Alan Jackson | 14 |
| 6 | 6 | Amazed Lonestar | 19 |
| 7 | 9 | What Do You Say To That George Strait | 6 |
| 8 | 8 | Lesson In Leavin' Jo Dee Messina | 19 |
| 9 | 13 | I'm Already Taken Steve Wariner | 5 |
| 10 | 10 | I'll Still Love You More Trisha Yearwood | 11 |
| 11 | 7 | The Secret Of Life Faith Hill | 15 |
| 12 | 14 | She's In Love Mark Wills | 7 |
| 13 | 15 | Lonely And Gone Montgomery Gentry | 5 |
| 14 | 16 | Home To You John Michael Montgomery | 3 |
| 15 | 12 | (Now You See Me) Now You Don't Lee Ann Womack | 10 |
| 16 | 18 | I'll Go Crazy Andy Griggs | 4 |
| 17 | 19 | Missing You Brooks & Dunn | 2 |
| 18 | - | When I Said I Do Clint Black w/ Lisa Hartman-Black | 1 |
| 19 | 17 | Write This Down George Strait | 24 |
| 20 | 20 | Make Up In Love Doug Stone | 3 |