1999-12-04 — CKX 1150 AM ( Brandon, Manitoba )
| TW | LW | | ARTIST | TITLE | WKS |
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| 4 | | | Yankee Grey | All Things Considered | | | 6 | | | Tim McGraw | My Best Friend | | | 2 | | | Martina McBride | I Love You | | | PH | | | Lonestar | Smile | | | 3 | | | Kenny Chesney | She Thinks My Tractor's Sexy | | | 10 | | | Julian Austin | Back In Your Life | | | 7 | | | John Michael Montgomery | Home To You | | | 5 | | | Faith Hill | Breathe | | | 1 | | | Dixie Chicks | Cowboy Take Me Away | | | 9 | | | Clint Black (With Lisa Hartman Black) | When I Said I Do | | | 8 | | | Brad Paisley | He Didn't Have To Be | |
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