St. Valentine's Day Massacre: In Your House was the 27th In Your House pay-per-view from the World Wrestling Federation (WWF). It took place on February 14, 1999, at The Pyramid in Memphis, Tennessee. The title of the event alludes to the Saint Valentine's Day massacre of 1929, which saw seven people murdered as part of the gang war between Al Capone and Bugs Moran. The event saw the WWF debut of Big Show, who was referred to by his real name, Paul Wight, during the event.

Eight professional wrestling matches were scheduled on the event's card. The first main event was that of the WWF Championship. As The Rock and Mankind had fought many times previously with ambiguous match endings, it was decided the match would be a Last Man Standing match, a match where a wrestler loses if they cannot stand up before the referee counts to ten. The second main event was a steel cage match between Steve Austin and the owner of the company, Vince McMahon, to decide whether Austin would go on to headline WrestleMania XV the following month.

The leader of The J.O.B. Squad, Al Snow had his mascot, a mannequin head he believed to be sentient, stolen from him by Goldust who restyled the head in keeping with his own make up style. In a match on the edition of January 25 of Raw is War, The Blue Meanie made his WWF debut by coming through the crowd and stealing the head back for Snow. The following week on February 1, Goldust attacked Blue Meanie but the night before the event, on a special Saturday Night Raw, Goldust lost a match to perennial jobber Gillberg when Meanie distracted him with a video parodying the wrestler, renaming himself Bluedust. After the match was over the arena went dark with a blue hue, similar to Goldust's effect of a gold hue, and Goldust had been disgraced by having blue paint poured over him.

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