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On Monday night, Boston Red Sox first baseman Willson Contreras will do something that no Red Sox batter has done in 15 years: participate in the Home Run Derby. Contreras will join Jim Rice, Mo Vaughn, Nomar Garciaparra, Carl Everett, David Ortiz, and Adrian Gonzalez as Boston sluggers to participate in the Derby.
With Contreras set to participate, we look back at how some Red Sox players have fared in the annual showcase.
It should come as no surprise that the Hall of Fame designated hitter leads the Red Sox in Home Run Derby participation since he arrived in Boston in 2003. In his 14 years in Boston, Ortiz participated in the Derby on five different occasions.
After hitting 23 home runs ahead of the All-Star game in Houston’s Minute Maid Park, Ortiz participated in the first Home Run Derby of his career, entering a loaded field that featured sluggers like Barry Bonds, Miguel Tejada, Sammy Sosa, and Jim Thome.
Ortiz did not fare well in his first trip to the contest, getting eliminated after hitting the fewest home runs in round one (3).
It was Tejada who went on to win the Derby, hitting 27 home runs over the three rounds and defeating the hometown hero, Lance Berkman, in the process.
Ortiz, fresh off his disappointing performance the year prior, re-entered the Derby in 2005 at Detroit’s Comerica Park. The 29-year-old put together a much better performance than his first appearance, hitting 17 home runs in his first round of swings, good for second in the field behind only Bobby Abreu, who hit 24.
However, Ortiz’s night once again ended in disappointment, as he hit only three in his second round of swings, failing to advance to the finals.
Jul 10, 2006; Pittsburgh, PA, USA; American League All-Star player David Ortiz hits a home run during the Home Run Derby at PNC Park in Pittsburgh, PA. Scott Rovak-Imagn Images Copyright © 2006 Scott Rovak
The Hall of Famer made it three Derbies in a row in 2006, this time heading to Pittsburgh’s PNC Park.
Ortiz again failed to advance to the finals, this time hitting 13 home runs in his first two rounds of swings, just shy of the 18 hit by the two finalists, David Wright of the Mets and the eventual winner, Philadelphia’s Ryan Howard.
July 12, 2010; Anaheim, CA, USA; American League designated hitter David Ortiz of the Boston Red Sox hoists the trophy after winning the 2010 All Star home run derby at Angel Stadium. Scott Rovak-Imagn Images
After four seasons away from the Derby, Ortiz returned to the contest in 2010 at Anaheim’s Angel Stadium, delivering one of the best Derby performances of all-time en route to his lone Home Run Derby win.
Ortiz, along with former Red Sox farmhand Hanley Ramirez, hit 21 home runs in the first two rounds to advance to the final round. Ortiz once again lapped the competition, defeating his future teammate 11-5 to claim the championship.
Ortiz’s final Home Run Derby came at Arizona’s Chase Field as part of the 2011 All-Star Game festivities, where he would seek to defend his title.
July 11, 2011; Phoenix, AZ, USA; American League player David Ortiz (34) of the Boston Red Sox is greeted by teammate Adrian Gonzalez during the 2011 home run derby at Chase Field. Mark J. Rebilas-Imagn Images
The then-35-year-old was eliminated after the first two rounds of the tournament, hitting only nine home runs, well shy of the 20 hit by the two finalists, Red Sox teammate Adrian Gonzalez and Yankees second baseman Robinson Cano, the latter of whom went on to claim the title.
Ortiz was joined in the 2011 Derby by teammate first baseman Adrian Gonzalez, who hit 17 home runs leading up to the All-Star break in his first season in Boston.
The 29-year-old Gonzalez performed well in his first appearance in the Derby, hitting 20 long balls in the first two rounds, tying Cano for the most to advance to the finals.
July 11, 2011; Phoenix, AZ, USA; American League first baseman Adrian Gonzalez (28) of the Boston Red Sox during the final round of the 2011 home run derby at Chase Field. Scott Rovak-Imagn Images
However, it was Cano who edged out the Boston first baseman, hitting 12 homers to Gonzalez’s 11 to claim the 2011 Home Run Derby crown.
Contreras will look to become the first Red Sox hitter to claim a Home Run Derby crown since Ortiz in 2010 on Monday night at Citizens Bank Park in Philadelphia. Festivities get underway at 8:00 p.m. ET on Netflix.
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With Contreras set to participate, we look back at how some Red Sox players have fared in the annual showcase.
Willson Contreras is ready to take a bite out of the competition and win the @TMobile#HRDerby! pic.twitter.com/rhvvgB8oyr
— MLB (@MLB) July 13, 2026
David Ortiz
It should come as no surprise that the Hall of Fame designated hitter leads the Red Sox in Home Run Derby participation since he arrived in Boston in 2003. In his 14 years in Boston, Ortiz participated in the Derby on five different occasions.
Throwback to David Ortiz winning the Home Run Derby back in 2010!
He smashed 8 homers in the first round, 13 in the second, and 11 more in the finals.
Hanley Ramirez was the runner-up.#RedSox | #DirtyWater| #MLBpic.twitter.com/WPHaWNDt4q
— Tyler Milliken (@tylermilliken_) July 18, 2022
2004
After hitting 23 home runs ahead of the All-Star game in Houston’s Minute Maid Park, Ortiz participated in the first Home Run Derby of his career, entering a loaded field that featured sluggers like Barry Bonds, Miguel Tejada, Sammy Sosa, and Jim Thome.
Ortiz did not fare well in his first trip to the contest, getting eliminated after hitting the fewest home runs in round one (3).
It was Tejada who went on to win the Derby, hitting 27 home runs over the three rounds and defeating the hometown hero, Lance Berkman, in the process.
2005
Ortiz, fresh off his disappointing performance the year prior, re-entered the Derby in 2005 at Detroit’s Comerica Park. The 29-year-old put together a much better performance than his first appearance, hitting 17 home runs in his first round of swings, good for second in the field behind only Bobby Abreu, who hit 24.
However, Ortiz’s night once again ended in disappointment, as he hit only three in his second round of swings, failing to advance to the finals.
2006
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Jul 10, 2006; Pittsburgh, PA, USA; American League All-Star player David Ortiz hits a home run during the Home Run Derby at PNC Park in Pittsburgh, PA. Scott Rovak-Imagn Images Copyright © 2006 Scott Rovak
The Hall of Famer made it three Derbies in a row in 2006, this time heading to Pittsburgh’s PNC Park.
Ortiz again failed to advance to the finals, this time hitting 13 home runs in his first two rounds of swings, just shy of the 18 hit by the two finalists, David Wright of the Mets and the eventual winner, Philadelphia’s Ryan Howard.
2010
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July 12, 2010; Anaheim, CA, USA; American League designated hitter David Ortiz of the Boston Red Sox hoists the trophy after winning the 2010 All Star home run derby at Angel Stadium. Scott Rovak-Imagn Images
After four seasons away from the Derby, Ortiz returned to the contest in 2010 at Anaheim’s Angel Stadium, delivering one of the best Derby performances of all-time en route to his lone Home Run Derby win.
Ortiz, along with former Red Sox farmhand Hanley Ramirez, hit 21 home runs in the first two rounds to advance to the final round. Ortiz once again lapped the competition, defeating his future teammate 11-5 to claim the championship.
2011
Ortiz’s final Home Run Derby came at Arizona’s Chase Field as part of the 2011 All-Star Game festivities, where he would seek to defend his title.
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July 11, 2011; Phoenix, AZ, USA; American League player David Ortiz (34) of the Boston Red Sox is greeted by teammate Adrian Gonzalez during the 2011 home run derby at Chase Field. Mark J. Rebilas-Imagn Images
The then-35-year-old was eliminated after the first two rounds of the tournament, hitting only nine home runs, well shy of the 20 hit by the two finalists, Red Sox teammate Adrian Gonzalez and Yankees second baseman Robinson Cano, the latter of whom went on to claim the title.
Adrian Gonzalez
Ortiz was joined in the 2011 Derby by teammate first baseman Adrian Gonzalez, who hit 17 home runs leading up to the All-Star break in his first season in Boston.
The 29-year-old Gonzalez performed well in his first appearance in the Derby, hitting 20 long balls in the first two rounds, tying Cano for the most to advance to the finals.
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July 11, 2011; Phoenix, AZ, USA; American League first baseman Adrian Gonzalez (28) of the Boston Red Sox during the final round of the 2011 home run derby at Chase Field. Scott Rovak-Imagn Images
However, it was Cano who edged out the Boston first baseman, hitting 12 homers to Gonzalez’s 11 to claim the 2011 Home Run Derby crown.
Contreras will look to become the first Red Sox hitter to claim a Home Run Derby crown since Ortiz in 2010 on Monday night at Citizens Bank Park in Philadelphia. Festivities get underway at 8:00 p.m. ET on Netflix.
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Remember to join our RED SOX on ROUNDTABLE community, which is FREE! You can post your own thoughts, in text or video form, and you can engage with our Roundtable staff, as well as other Red Sox fans. If prompted to download the Roundtable APP, that's free too!
Continue reading...