The 1999 Over the Edge was the second annual and final Over the Edge professional wrestling pay-per-view (PPV) event produced by the World Wrestling Federation (WWF, renamed to WWE in 2002). It was held on May 23, 1999, at Kemper Arena in Kansas City, Missouri. The first Over the Edge event was held under the In Your House series in May 1998, but following the discontinuation of the In Your House shows, a second Over the Edge event was scheduled as its own PPV, thus being the first former In Your House event to do so.

In the main event, The Undertaker faced Stone Cold Steve Austin in a singles match (with Vince McMahon and Shane McMahon as the guest referees) for the WWF Championship. Of the six scheduled bouts on the undercard, two received more promotion than the other matches. The first was a singles match, in which The Rock defeated Triple H by disqualification. The other was an eight-man elimination tag team match in which The Union (Mankind, Ken Shamrock, Test, and Big Show) defeated the Corporate Ministry (Viscera, Big Boss Man, and the Acolytes (Bradshaw and Faarooq)).

The event is infamous for the fatal accident involving wrestler Owen Hart, who was scheduled to face The Godfather for the WWF Intercontinental Championship during the event. Wrestling under his Blue Blazer gimmick, Hart was to make a superhero-like ring entrance, which would have seen him descend from the arena rafters into the ring. He was, however, released prematurely when the harness line malfunctioned, and fell more than 78 feet (24 m) into the ring and died. Criticism later arose over Vince McMahon's decision to continue the show after Hart's accident. In court, his widow Martha, children, and parents sued the organization, contending that poor planning of the dangerous stunt caused Owen's death. WWF settled the case out of court, with the McMahon family paying US$18 million (equivalent to $31 million in 2022) to his widow, children, and parents. Due to the accident and controversy surrounding the event, the Over the Edge name was retired and its PPV slot was replaced by Judgment Day in 2000. The event was also not released for home video viewing until the launch of the WWE Network in 2014 where an edited version of the show removing any mention of Hart's death was released.