Chicago Cubs
On May 11, 2000, Glenallen Hill, facing Brewers starter Steve Woodard, became the first, and thus far only player, to hit a pitched ball onto the roof of a five-story residential building across Waveland Ave, beyond Wrigley Field's left field wall. The shot was estimated at well over 500 feet (150 m), but the Cubs fell to Milwaukee 12–8. No batted ball has ever hit the center field scoreboard, although the original "Slammin' Sammy", golfer Sam Snead, hit it with a golf ball in an exhibition in the 1950s. In 1948, Bill Nicholson barely missed the scoreboard when he launched a home run ball onto Sheffield Avenue and in 1959, Roberto Clemente came even closer with a home run ball hit onto Waveland Avenue. In 2001, a Sammy Sosa shot landed across Waveland and bounced a block down Kenmore Avenue. Dave Kingman hit a shot in 1979 that hit the third porch roof on the east side of Kenmore, estimated at 555 feet (169 m), and is regarded as the longest home run in Wrigley Field history. On May 26, 2015, the Cubs rookie third baseman, Kris Bryant, hit a homerun that traveled an estimated 477 feet (145 m) off the park's new videoboard in left field. Later the same year, he hit a homer that traveled 495 feet (151 m) that also ricocheted off of the videoboard On October 13, 2015, Kyle Schwarber's 438-foot home run landed on the equally new right field videoboard.

Q: When did the first and only player to hit a pitched ball onto the roof of a five-story building across Waveland Ave?
May 11, 2000