The October 21, 1999 Edition of Smackdown is a Professional wrestling television show of the WWF's Smackdown brand. It was taped on October 19, 1999 at Freedom Hall in Louisville, Kentucky.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Included Mankind cutting an in-ring promo to begin the show in which he made mention of his book, Have a Nice Day, saying it was the greatest thing he ever did.
- Moments later, Mankind did a sit-in to get Vince McMahon's attention and, after Vince came out, Mankind said he wanted a title shot and wanted to beat the Rock in order to earn it.
- The Rock then came out and accepted the challenge.
- After Mankind left the ring, Rock confronted Vince and said that if he was wrestling tonight, Steve Austin should be wrestling as well.
- When Vince said no one had challenged Austin, Val Venis came out and did so.
- Austin came out, accepted the challenge, and sent Venis out of the ring as Vince and Rock left ringside.
- Featured footage of Mark Henry at his 5th sex therapist in which his therapist was revealed to be the Godfather, with Godfather telling Henry there was absolutely nothing wrong with him.