On March 9, 2017, MLB officially announced the first MLB Little League Classic, selecting the Pittsburgh Pirates and St. Louis Cardinals as the participants, and released the following statement:
Major League Baseball's greatest responsibility is to ensure that today's youth become active participants in our game as players and fans. The 'MLB Little League Classic' exemplifies our entire sport's commitment to building a stronger connection between young people and the National Pastime. Our players will honor the great tradition of the Little League World Series and create lifelong memories for the Little Leaguers, their families and the city of Williamsport. I thank the Pirates and the Cardinals, Little League Baseball, Governor Wolf, the Crosscutters, the City of Williamsport, and ESPN for helping us organize an unforgettable weekend.
— The Pirates defeated the Cardinals, 6–3, in the first Classic, played on August 20, 2017. Residents from Lycoming County were eligible to win a very limited number of tickets to the game via a lottery system found on the MLB website. The game was originally scheduled to be a home game for the Pirates; ticket holders for that game were offered a food-and-beverage credit, tickets to another game, or a refund. The Cardinals and Pirates wore special uniforms, including features such as pullover jerseys with bright colors and contrasting sleeves, specially colored caps, and a unique logo that drew design cues from the official logos of both MLB and Little League Baseball. In addition, players were encouraged (although not required) to put nicknames on the jerseys' rear nameplates. These uniforms were worn again by both teams on August 25–27 for Players Weekend, an initiative of MLB and the Major League Baseball Players Association that saw all 30 MLB teams wear similar uniforms.
In late September 2017, MLB announced that a second Classic would be held in 2018, between the New York Mets and Philadelphia Phillies. On August 19, 2018, the Mets won the second Classic, 8–2. The Phillies had last played at Bowman Field on July 31, 1962, when the team lost to the Williamsport Grays, the Phillies' Eastern League affiliate, in a mid-season exhibition game.
The Red Sox and Orioles, originally scheduled to play during the 2020 season, played the fifth edition of the Classic on August 21, 2022. The teams wore standard uniforms. The Orioles won the game, 5–3, largely powered by a three-run double in the bottom of the eighth inning by Jorge Mateo.
"ESPN to cover MLB Little League Classic August 20 in Williamsport". sportsvideo.org. March 10, 2017. http://www.sportsvideo.org/2017/03/10/espns-sunday-night-baseball-to-host-mlb-little-league-classic/
"Pirates and Cardinals will attend the Little League games during the day and the little leaguers will attend the Major League game at night". WTAE-TV. March 9, 2017. Retrieved April 4, 2017. http://www.wtae.com/article/pirates-and-cardinals-to-play-mlb-little-league-classic/9112450
Goold, Derrick (March 7, 2017). "Williamsport Calling". St. Louis Post-Dispatch. Retrieved August 20, 2017 – via Newspapers.com. https://www.newspapers.com/clip/13216150/williamsport_calling/
"Cardinals and Pirates have been selected to participate in the first "MLB Little League Classic"". St. Louis Post-Dispatch. March 9, 2017. Retrieved April 4, 2017. http://www.stltoday.com/sports/baseball/professional/birdland/cardinals-pirates-set-to-play-in-the-mlb-little-league/article_c9b780b9-062e-5f00-a126-83b666f96be7.html
"Major League Baseball has officially announced that the Pirates and Cardinals will take the field on August 20th in Williamsport". KDKA-TV. March 9, 2017. Retrieved April 4, 2017. http://pittsburgh.cbslocal.com/2017/03/09/pirates-to-play-cardinals-in-mlb-little-league-classic/
"MLB ANNOUNCES LITTLE LEAGUE CLASSIC". Baseball America. March 9, 2017. Retrieved April 4, 2017. http://www.baseballamerica.com/business/mlb-announces-little-league-classic/#4YvuIfMvd4dT0st7.97
"Crosscutters Baseball Field Gets Upgrade Thanks to MLB". WNEP-TV. April 4, 2017. Retrieved April 4, 2017. http://wnep.com/2017/04/03/crosscutters-baseball-field-gets-upgrade-thanks-to-mlb/
"Cardinals vs. Pirates - Game Summary". ESPN. August 20, 2017. Retrieved August 8, 2019. https://www.espn.com/mlb/game?gameId=370820123
Beauge, John (June 15, 2017). "Lycoming County residents can win free tickets to Aug. 20 Pirates-Cards game in Williamsport". pennlive.com. http://www.pennlive.com/little-league-world-series/2017/06/lycoming_county_residents_can.html
Brink, Bill (March 9, 2017). "Pirates and Cardinals will play a game in Williamsport". Pittsburgh Post-Gazette. Retrieved August 20, 2017. http://www.post-gazette.com/sports/pirates/2017/03/09/MLB-MLBPA-make-official-Pirates-Cardinals-game-in-Williamsport/stories/201703090166
Lukas, Paul (August 9, 2017). "It's uniform change for MLB's Players Weekend". Uni Watch. ESPN.com. Retrieved August 9, 2017. https://www.espn.com/mlb/story/_/id/20294267/mlb-get-whole-new-look-teams-take-field-end-august
Trezza, Joe (September 29, 2017). "Phils, Mets to play in MLB Little League Classic". MLB.com. MLB Advanced Media. Retrieved April 24, 2018. https://www.mlb.com/news/phils-mets-to-play-in-little-league-classic/c-256548822
"Mets vs. Phillies - Game Summary". ESPN. August 19, 2018. Archived from the original on April 12, 2018. Retrieved August 8, 2019. https://web.archive.org/web/20180412091113/http://www.espn.com/mlb/game?gameId=380819122
"Williamsport Scores 4 In 1st to Whip Phillies". The Philadelphia Inquirer. Philadelphia, Pennsylvania. August 1, 1962. p. 32. https://www.newspapers.com/clip/64056747/williamsport-scores-4-in-1st-to-whip/
Randhawa, Manny (August 19, 2018). "Bucs, Cubs to match up in 2019 LL Classic". MLB.com. Retrieved August 20, 2018. https://www.mlb.com/news/2019-little-league-classic-is-pirates-vs-cubs/c-291092642
"Quintana, Rizzo lead Cubs past Pirates 7-1 at LLWS". AP. August 18, 2019. Retrieved August 18, 2019. https://www.espn.com/mlb/recap?gameId=401076602
Bell, Demetrius (August 9, 2019). "MLB Continues The Spirit Of Previous Players' Weekend Uniforms With 2019 Little League Classic Uniforms". Forbes. Retrieved January 10, 2023. https://www.forbes.com/sites/demetriusbell/2019/08/09/mlb-continues-the-spirit-of-previous-players-weekend-uniforms-with-2019-little-league-classic-uniforms/?sh=777d289a54f6
"Red Sox, O's to play in '20 Little League Classic". MLB.com (Press release). August 7, 2019. Retrieved August 7, 2019. https://www.mlb.com/news/red-sox-orioles-to-play-in-2020-little-league-classic
"Little League® Cancels 2020 World Series and Region Tournaments" (Press release). Little League Baseball. April 30, 2020. Retrieved April 30, 2020. https://www.littleleague.org/news/little-league-cancels-2020-world-series-and-region-tournaments/
"Angels, Indians in 2021 LL Classic". St. Louis Post-Dispatch. August 24, 2020. p. B4. Retrieved August 29, 2022 – via newspapers.com. https://www.newspapers.com/clip/108563178/angels-indians-in-2021-ll-classic/
"Red Sox, O's set for '22 Little League Classic". MLB.com. August 22, 2021. Retrieved August 22, 2021. https://www.mlb.com/news/red-sox-orioles-to-play-2022-little-league-classic
"The 2020 Baltimore Orioles Regular Season Game Log". Retrosheet. Retrieved August 29, 2022. https://www.retrosheet.org/boxesetc/2020/VBAL02020.htm
Reichard, Kevin (August 23, 2020). "Williamsport Little League Classic announced for 2021 season". Ballpark Digest. August Publications. https://ballparkdigest.com/2020/08/23/williamsport-little-league-classic-announced-for-2021-season/
Bell, Mandy (August 22, 2021). "Cal, Cleveland cruise vs. Halos at LL Classic". MLB.com. Retrieved August 22, 2021. https://www.mlb.com/news/cal-quantrill-leads-shutout-of-angels-at-little-league-classic
Bell, Mandy (August 20, 2021). "Little League Classic FAQ: Angels vs. Indians". MLB.com. Retrieved August 21, 2021. https://www.mlb.com/news/angels-indians-little-league-classic-2021-faq
"MLB Little League Classic to Welcome the Los Angeles Angels and Cleveland Indians to Williamsport in 2021". MLB.com. June 16, 2021. Retrieved June 18, 2021. https://www.littleleague.org/news/mlb-little-league-classic-to-welcome-the-los-angeles-angels-and-cleveland-indians-to-williamsport-in-2021/
"Red Sox, O's set for '22 Little League Classic". MLB.com. August 22, 2021. Retrieved August 22, 2021. https://www.mlb.com/news/red-sox-orioles-to-play-2022-little-league-classic
Benbow, Julian (August 21, 2022). "Bullpen blowup leaves sour taste for Red Sox as Orioles win Little League Classic". The Boston Globe. Retrieved August 21, 2022. https://www.bostonglobe.com/2022/08/21/sports/bullpen-blowup-leaves-sour-taste-red-sox-orioles-win-little-league-classic/
Zolecki, Todd (August 21, 2022). "Phils, Nats to face off in '23 Little League Classic". mlb.com. MLB Advanced Media. Retrieved August 22, 2022. https://www.mlb.com/phillies/news/phillies-nationals-to-play-in-2023-little-league-classic
Camerato, Jessica (August 20, 2023). "Nats cap special day in Williamsport with a victory". MLB.com. Retrieved August 23, 2023. https://www.mlb.com/news/nationals-beat-phillies-in-little-league-classic
"Yankees, Tigers to face off in 2024 Little League Classic". MLB.com. August 20, 2023. https://www.mlb.com/news/yankees-tigers-to-play-in-2024-little-league-classic
"Parker Meadows gives Tigers 3-2 walk-off win over Yankees in MLB Little League Classic". detroitnews.com. AP. August 18, 2024. Retrieved August 19, 2024. https://www.detroitnews.com/story/sports/mlb/tigers/2024/08/18/detroit-tigers-new-york-yankees-little-league-classic/74850680007/
Kramer, Daniel (August 18, 2024). "Mariners, Mets to face off in 2025 Little League Classic". MLB.com. Retrieved August 19, 2024. https://www.mlb.com/mariners/news/mariners-mets-to-play-in-2025-little-league-classic
Kramer, Daniel (August 18, 2024). "Mariners, Mets to face off in 2025 Little League Classic". MLB.com. Retrieved August 19, 2024. https://www.mlb.com/mariners/news/mariners-mets-to-play-in-2025-little-league-classic
"Pittsburgh Pirates 6, St. Louis Cardinals 3". Retrosheet. August 20, 2017. Retrieved August 7, 2019. https://www.retrosheet.org/boxesetc/2017/B08200PIT2017.htm
"New York Mets 8, Philadelphia Phillies 2". Retrosheet. August 19, 2018. Retrieved August 7, 2019. https://www.retrosheet.org/boxesetc/2018/B08190PHI2018.htm
"Cubs 7-1 Pirates". ESPN.com. August 18, 2019. Retrieved August 18, 2019. https://www.espn.com/mlb/boxscore?gameId=401076602
"Cleveland Indians 3, Anaheim Angels 0". Retrosheet. August 22, 2021. Retrieved May 9, 2022. https://www.retrosheet.org/boxesetc/2021/B08220CLE2021.htm
"Orioles 5-3 Red Sox". ESPN.com. August 21, 2022. Retrieved August 21, 2022. https://www.espn.com/mlb/boxscore/_/gameId/401356024
"Washington Nationals 4, Philadelphia Phillies 3". ESPN.com. August 20, 2023. Retrieved August 20, 2023. https://www.espn.com/mlb/game/_/gameId/401472879
"Tigers 3-2 Yankees". ESPN.com. August 18, 2024. Retrieved August 19, 2024. https://www.espn.com/mlb/boxscore/_/gameId/401570333
Kramer, Daniel (August 18, 2024). "Mariners, Mets to face off in 2025 Little League Classic". MLB.com. Retrieved August 19, 2024. https://www.mlb.com/mariners/news/mariners-mets-to-play-in-2025-little-league-classic
"ESPN to broadcast MLB Little League Classic in Williamsport PA". ESPN Media Ventures, LLC. March 11, 2017. Retrieved April 4, 2017. http://espnmediazone.com/us/press-releases/2017/03/espn-exclusively-televise-mlb-little-league-classic-sunday-night-baseball/
Skarka, Michael (August 14, 2018). "ESPN Plans Full Day of Coverage Culminating with MLB Little League Classic on Sunday Night Baseball August 19". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2018/08/espn-plans-full-day-of-coverage-culminating-with-mlb-little-league-classic-on-sunday-night-baseball-august-19/
Bastian, Jordan; Berry, Adam (August 18, 2019). "Every Little League Classic question, answered". MLB.com. Retrieved May 8, 2022. https://www.mlb.com/news/pirates-cubs-2019-little-league-classic-faq
Hughes, Katie (August 18, 2021). "ESPN to Provide Exclusive Coverage of the 2021 MLB Little League Classic on Sunday Night Baseball Presented by Taco Bell Featuring the Los Angeles Angels vs. Cleveland Indians". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2021/08/espn-to-provide-exclusive-coverage-of-the-2021-mlb-little-league-classic-on-sunday-night-baseball-presented-by-taco-bell-featuring-the-los-angeles-angels-vs-cleveland-indians/
Hughes, Katie (March 17, 2022). "Play Ball! 2022 ESPN Sunday Night Baseball Presented by Taco Bell Schedule Opens April 10 with Boston Red Sox at New York Yankees". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2022/03/play-ball-2022-espn-sunday-night-baseball-presented-by-taco-bell-schedule-opens-april-10-with-boston-red-sox-at-new-york-yankees/
Panitz, Bea (August 15, 2023). "On Deck: Philadelphia Phillies play Washington Nationals in the 2023 MLB Little League Classic". espnpressroom.com (Press release). Retrieved August 17, 2023. https://espnpressroom.com/us/press-releases/2023/08/on-deck-philadelphia-phillies-play-washington-nationals-in-the-2023-mlb-little-league-classic/
Feuz, Alex (August 2024). "Headed to Williamsport: ESPN Platforms Begin Exclusive Coverage of 2024 Little League Baseball World Series, Presented by T-Mobile". espnpressroom.com/ (Press release). Retrieved August 19, 2024. https://espnpressroom.com/us/press-releases/2024/08/headed-to-williamsport-espn-platforms-begin-exclusive-coverage-of-2024-little-league-baseball-world-series-presented-by-t-mobile/
Cafardo, Ben (August 16, 2017). "ESPN to Provide Comprehensive Coverage of MLB Little League Classic on Sunday Night Baseball". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2017/08/espn-provide-comprehensive-coverage-mlb-little-league-classic-sunday-night-baseball/
Skarka, Michael (August 14, 2018). "ESPN Plans Full Day of Coverage Culminating with MLB Little League Classic on Sunday Night Baseball August 19". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2018/08/espn-plans-full-day-of-coverage-culminating-with-mlb-little-league-classic-on-sunday-night-baseball-august-19/
Hughes, Katie (August 15, 2019). "ESPN To Exclusively Televise Third Annual MLB Little League Classic Presented By GEICO on Sunday Night Baseball: Chicago Cubs vs. Pittsburgh Pirates". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2019/08/espn-to-exclusively-televise-third-annual-mlb-little-league-classic-presented-by-geico-on-sunday-night-baseball-chicago-cubs-vs-pittsburgh-pirates/
Hughes, Katie (August 18, 2021). "ESPN to Provide Exclusive Coverage of the 2021 MLB Little League Classic on Sunday Night Baseball Presented by Taco Bell Featuring the Los Angeles Angels vs. Cleveland Indians". espnpressroom.com (Press release). Retrieved May 8, 2022. https://espnpressroom.com/us/press-releases/2021/08/espn-to-provide-exclusive-coverage-of-the-2021-mlb-little-league-classic-on-sunday-night-baseball-presented-by-taco-bell-featuring-the-los-angeles-angels-vs-cleveland-indians/
Rajan, Ronce (August 18, 2022). "ESPN to Exclusively Televise 2022 MLB Little League Classic Presented by GEICO – Boston Red Sox vs. Baltimore Orioles – on August 21 Sunday Night Baseball". espnpressroom.com. Retrieved August 21, 2022. https://espnpressroom.com/us/press-releases/2022/08/espn-to-exclusively-televise-2022-mlb-little-league-classic-presented-by-geico-boston-red-sox-vs-baltimore-orioles-on-august-21-sunday-night-baseball/
Panitz, Bea (August 15, 2023). "On Deck: Philadelphia Phillies play Washington Nationals in the 2023 MLB Little League Classic". espnpressroom.com (Press release). Retrieved August 17, 2023. https://espnpressroom.com/us/press-releases/2023/08/on-deck-philadelphia-phillies-play-washington-nationals-in-the-2023-mlb-little-league-classic/
Feuz, Alex (August 2024). "Headed to Williamsport: ESPN Platforms Begin Exclusive Coverage of 2024 Little League Baseball World Series, Presented by T-Mobile". espnpressroom.com/ (Press release). Retrieved August 19, 2024. https://espnpressroom.com/us/press-releases/2024/08/headed-to-williamsport-espn-platforms-begin-exclusive-coverage-of-2024-little-league-baseball-world-series-presented-by-t-mobile/