Winter Break was recorded at the Bayfront Park Amphitheater in Miami, Florida on January 17, 1999, for a crowd of 10,000 people. During the show, Twain received special guests Elton John, the Backstreet Boys and Leahy onstage. The special features scenes of Twain visiting her hometown Timmins, Ontario in between songs. It aired on March 3, 1999 on CBS, attracting ratings of 10.3 points, about 18.7 million viewers.
| Actor | Role |
|---|---|
 Shania TwainSelf | Self |
 Elton JohnSelf | Self |
 AJ McLeanSelf | Self |
 Howie DoroughSelf | Self |
 Nick CarterSelf | Self |
 Kevin RichardsonSelf | Self |
 Brian LittrellSelf | Self |