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Country Radio Top 20 | |||
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8/27/1999 | |||
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| 1 | 1 | Amazed Lonestar | 14 |
| 2 | 2 | Lesson In Leavin' Jo Dee Messina | 14 |
| 3 | 4 | Single White Female Chely Wright | 12 |
| 4 | 6 | You Had Me From Hello Kenny Chesney | 9 |
| 5 | 3 | (God Must Have Spent) A Little More Time On You Alabama | 15 |
| 6 | 7 | The Secret Of Life Faith Hill | 10 |
| 7 | 8 | Little Man Alan Jackson | 9 |
| 8 | 5 | Little Good-Byes SheDaisy | 13 |
| 9 | 11 | Something Like That Tim McGraw | 4 |
| 10 | 9 | Ready To Run Dixie Chicks | 6 |
| 11 | 12 | Write This Down George Strait | 19 |
| 12 | 15 | I'll Still Love You More Trisha Yearwood | 6 |
| 13 | 18 | I Love You Martina McBride | 3 |
| 14 | 10 | A Night To Remember Joe Diffie | 14 |
| 15 | 16 | (Now You See Me) Now You Don't Lee Ann Womack | 5 |
| 16 | 14 | You've Got A Way Shania Twain | 7 |
| 17 | 13 | Who Needs Pictures Brad Paisley | 10 |
| 18 | 17 | This Heartache Never Sleeps Mark Chesnutt | 6 |
| 19 | - | What Do You Say To That George Strait | 1 |
| 20 | 20 | She's In Love Mark Wills | 2 |