The World Baseball Classic has already delivered its share of surprises this March, and Monday night’s semifinal between Italy and Venezuela might be one of the most intriguing matchups yet.

Italy enters the game as one of the breakout stories of the tournament.

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They’re a perfect 5-0 so far, knocking off the United States and two-time WBC runner-up Puerto Rico while blasting their way through the bracket with one of the most dangerous offenses in the field.

Italy has hit the second-most home runs in the tournament and carries a .982 team OPS into the semifinals, turning a roster full of overlooked hitters into one of the most entertaining lineups in the event.

Venezuela, meanwhile, is back in the semifinals for the first time since 2009.

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Powered by stars like Ronald Acuna Jr., Luis Arraez and Maikel Garcia, the Venezuelan lineup has been one of the tournament’s most balanced groups. The club sits at 4-1 entering the matchup, highlighted by a dramatic quarterfinal victory over defending champion Japan that pushed Venezuela back into the tournament’s final four.

For the Boston Red Sox, the matchup also carries a little extra intrigue.

Several members of Boston’s organization are scattered across both rosters, meaning Red Sox fans will see familiar names on opposite sides of the semifinal stage.

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From rising prospects to established major leaguers, the game offers a unique look at how Boston’s international talent is performing under the spotlight of one of baseball’s biggest global events.

The stakes couldn’t be higher.

The winner will advance to Tuesday’s championship game in Miami with a chance to claim the 2026 WBC title against the United States.

Here are the five members of the Boston Red Sox spread across both Team Italy and Team Venezuela:

Wilyer Abreu, Venezuela

Few players in the tournament have delivered a bigger moment than Abreu. The Red Sox outfielder has been one of Venezuela’s most productive hitters, batting .294 with a .381 on-base percentage and 6 RBI through the team’s first five games. His defining moment came in the quarterfinals, when he crushed a 409-foot, three-run homer against Japan to flip the game and send Venezuela to the semifinals. The swing, punctuated by an emotional bat flip, instantly became one of the most memorable highlights of this year’s WBC run.

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Mar 14, 2026; Miami, FL, United States; Venezuela left fielder Wilyer Abreu (16) reacts while rounding the bases after hitting a three-run home run against Japan in the sixth inning during a quarterfinal game of the 2026 World Baseball Classic at loanDepot Park. (Sam Navarro/Imagn Images)

Mar 14, 2026; Miami, FL, United States; Venezuela left fielder Wilyer Abreu (16) reacts while rounding the bases after hitting a three-run home run against Japan in the sixth inning during a quarterfinal game of the 2026 World Baseball Classic at loanDepot Park. (Sam Navarro/Imagn Images)

Willson Contreras, Venezuela

Veteran slugger Contreras has provided another dangerous bat in Venezuela’s deep lineup throughout the tournament. While sharing catching duties with his brother William Contreras, the Red Sox first baseman has also spent time at designated hitter to keep his offense in the lineup. Contreras has delivered several timely hits during the tournament, including an RBI-single earlier in pool play against the Dominican Republic, helping Venezuela build momentum on its path to the semifinals.

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Willson Contreras signs a helmet for Oscar Mayeites before the Venezuela national baseball team played the Houston Astros in an exhibition game during the World Baseball Classic at CACTI Park of the Palm Beaches in West Palm Beach, Fla., on March 4, 2026. Astros won the game 3-1. (THOMAS CORDY/PALM BEACH POST/USA TODAY NETWORK/Imagn Images)

Willson Contreras signs a helmet for Oscar Mayeites before the Venezuela national baseball team played the Houston Astros in an exhibition game during the World Baseball Classic at CACTI Park of the Palm Beaches in West Palm Beach, Fla., on March 4, 2026. Astros won the game 3-1. (THOMAS CORDY/PALM BEACH POST/USA TODAY NETWORK/Imagn Images)

Mickey Gasper, Italy

The versatile Red Sox infielder joined Italy mid-tournament and has provided valuable depth during the club’s surprising WBC run. Gasper was added to the roster after former Red Sox prospect and starting catcher Kyle Teel suffered a hamstring injury, giving manager Francisco Cervelli another option behind the plate as Italy pushed into the knockout rounds. The call-up came on the heels of a strong spring training for Gasper, where he hit .364 with 2 home runs. While his role has primarily been defensive support and roster flexibility, his presence has helped stabilize Italy’s depth as the team chases a historic trip to the WBC title game.

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Ranger Suarez, Venezuela

Suarez has played an important role in Venezuela’s pitching staff during the World Baseball Classic, giving the club a steady left-handed presence in its rotation. The newest member of the Boston Red Sox – who signed a five-year, $130 million deal with the team this offseason – started multiple games during pool play and the knockout stage, including a quarterfinal appearance against Japan. Even in shorter outings typical of tournament play, Suarez has helped stabilize Venezuela’s staff as the team pushed its way back into the semifinals for the first time since 2009.

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Mar 14, 2026; Miami, FL, United States; Venezuela starting pitcher Ranger Suarez (55) delivers a pitch against Japan in the third inning during a quarterfinal game of the 2026 World Baseball Classic at loanDepot Park. (Sam Navarro/Imagn Images)

Mar 14, 2026; Miami, FL, United States; Venezuela starting pitcher Ranger Suarez (55) delivers a pitch against Japan in the third inning during a quarterfinal game of the 2026 World Baseball Classic at loanDepot Park. (Sam Navarro/Imagn Images)

Greg Weissert, Italy

The Red Sox reliever has emerged as one of the most important arms in Italy’s bullpen during the World Baseball Classic. Serving as the team’s closer, Weissert has been dominant in high-leverage moments, posting a 0.00 ERA with three saves across 3.1 innings. His biggest moment came in Italy’s upset win over the United States, when he worked out of a bases-loaded jam and struck out Aaron Judge to secure the victory. Weissert followed that with another clutch outing against Puerto Rico, recording a five-out save that helped send Italy to the semifinals and cemented his role as the team’s most trusted late-inning arm.

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Mar 14, 2026; Houston, TX, United States; Italy catcher JJ D'Orazio (28) and pitcher Greg Weissert (57) celebrate on the mound after the game against Puerto Rico during a quarterfinal game of the 2026 World Baseball Classic at Daikin Park. (Troy Taormina/Imagn Images)

Mar 14, 2026; Houston, TX, United States; Italy catcher JJ D’Orazio (28) and pitcher Greg Weissert (57) celebrate on the mound after the game against Puerto Rico during a quarterfinal game of the 2026 World Baseball Classic at Daikin Park. (Troy Taormina/Imagn Images)

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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He’s a senior digital content producer for WEEI.com, and a native of Lincoln, RI.