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Country Radio Top 20 | |||
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10/8/1999 | |||
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| 1 | 1 | Something Like That Tim McGraw | 10 |
| 2 | 2 | I Love You Martina McBride | 9 |
| 3 | 3 | Ready To Run Dixie Chicks | 12 |
| 4 | 9 | I'm Already Taken Steve Wariner | 6 |
| 5 | 7 | What Do You Say To That George Strait | 7 |
| 6 | 4 | You Had Me From Hello Kenny Chesney | 15 |
| 7 | 6 | Amazed Lonestar | 20 |
| 8 | 5 | Little Man Alan Jackson | 15 |
| 9 | 13 | Lonely And Gone Montgomery Gentry | 6 |
| 10 | 8 | Lesson In Leavin' Jo Dee Messina | 20 |
| 11 | 10 | I'll Still Love You More Trisha Yearwood | 12 |
| 12 | 14 | Home To You John Michael Montgomery | 4 |
| 13 | 12 | She's In Love Mark Wills | 8 |
| 14 | 16 | I'll Go Crazy Andy Griggs | 5 |
| 15 | 18 | When I Said I Do Clint Black w/ Lisa Hartman-Black | 2 |
| 16 | 17 | Missing You Brooks & Dunn | 3 |
| 17 | 11 | The Secret Of Life Faith Hill | 16 |
| 18 | - | Come On Over Shania Twain | 1 |
| 19 | - | Lightning Does The Work Chad Brock | 1 |
| 20 | - | He Didn't Have To Be Brad Paisley | 1 |