1999-05-22 — CICZ 104.1 FM ( Midland, Ontario )
| TW | LW | | ARTIST | TITLE | WKS | NOTES |
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| 1 | | | Martina McBride | Whatever You Say | | | | 2 | | | Tim McGraw | Please Remember Me | | | | 3 | | | Sawyer Brown | Drive Me Wild | | | | 4 | | | Alan Jackson | Gone Crazy | | | | 5 | | | George Strait | Write This Down | | | | 6 | | | Collin Raye | Anyone Else | | | | 7 | | | Dixie Chicks | Tonight The Heartache's On Me | | | | 8 | | | Steve Wariner | Two Teardrops | | | | 9 | | | Andy Griggs | You Won't Ever Be Lonely | | | | 10 | | | Stephanie Beaumont | Let's Do Something About It | | | | PH | | | Mark Chesnutt | This Heartache Never Sleeps | | |
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