When you're assembling a lineup of legends from throughout Boston Red Sox history to compete against 19 other teams that are also loaded with iconic Red Sox, it's a safe bet that any players emerging from the fray will be truly special.

A few months ago, WhatIfSports.com challenged 20 individuals to assemble 25-man rosters of present and past Boston greats. After a draft determined each team's rosters, the owners set lineups and rotations, competing in a 162-game simulated regular season in SimLeague Baseball. Ted Williams swept the NL and AL MVP awards (his 1942 and 1946 seasons, respectively), while 2000 Pedro Martinez and 1905 Cy Young proved to be the league's best pitchers. But it was 1988 Wade Boggs who led his team, the Blood Sox, to a World Series title.

Boggs' 1988 season was one of his best. The then-30-year-old posted a .366 batting average with a .476 OBP. In addition to 214 hits, he was walked 125 times, crossing home plate on 113 occasions. The Red Sox won the AL East in 1988 with an 89-73 record, but were swept in the ALCS by the Oakland A's.

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The simulated version of '88 Boggs would not suffer the same fate. His Blood Sox squad trailed 0-3 in the Division Series to MH On Huntington Ave II. With impending elimination on the line, the team fought back to tie the series and force a Game 7. Boggs was lethal in the rubber match, collecting five hits and four RBI as the Blood Sox cruised to a 20-11 blowout.

The World Series pitted the Blood Sox against the Curse of the Who?, a team that had overcome an 0-2 deficit to the Dirty Water in the Division Series before winning in six games. But luck was on the side of the Blood Sox in the Fall Classic, as the team won the series in five games to claim the championship hardware.

Check out the Blood Sox' full roster:

Pitchers
Player W-L SV IP ERA WHIP
2011 Daniel Bard 2-9 1 73.0 3.33 0.96
2015 Rich Hill 2-1 0 29.0 1.55 0.66
1944 Tex Hughson 18-5 5 203.1 2.26 1.05
1914 Dutch Leonard 19-5 3 224.2 0.96 0.89
2014 Andrew Miller 5-5 1 62.1 2.02 0.80
1912 Buck O'Brien 20-13 0 275.2 2.58 1.19
2011 Jonathan Papelbon 4-1 31 64.1 2.94 0.93
1914 Ernie Shore 10-5 1 139.2 2.00 0.98
1972 Luis Tiant 15-6 3 179.0 1.91 1.08
1907 George Winter 12-15 1 256.2 2.07 1.01
Catchers
Player R H RBI AVG OBP
1934 Rick Ferrell 50 130 48 .297 .390
Infield
Player R H RBI AVG OBP
1988 Wade Boggs 128 214 58 .366 .476
1942 Jimmie Foxx 43 69 33 .226 .320
1997 Jeff Frye 56 126 51 .312 .352
2003 Lou Merloni 24 48 18 .265 .355
1945 Skeeter Newsome 45 127 48 .290 .322
2010 Dustin Pedroia 53 87 41 .288 .367
Outfield
Player R H RBI AVG OBP
2005 Johnny Damon 117 197 75 .316 .366
1966 Don Demeter 43 87 41 .268 .284
1976 Fred Lynn 76 159 65 .314 .367
1968 Reggie Smith 78 148 69 .265 .342
1969 George Thomas 9 18 8 .353 .400
1931 Earl Webb 96 196 103 .333 .404
1953 Ted Williams 17 37 34 .407 .509
1966 Carl Yastrzemski 81 165 80 .278 .368

Try building your own SimLeague Baseball team, or assemble a Dream Team of your favorite players and simulate your squad against any MLB team in history.

For more from the Red Sox league, view our draft recap, first-round breakdown, All-Star break article or playoff preview.