​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.AdvertisementAdvertisementAdvertisementOrtiz 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.AdvertisementAdvertisementAdvertisementHowever, 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 RovakThe 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 ImagesAfter 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.AdvertisementAdvertisementAdvertisementOrtiz, 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