| NHL | ||||
| Year | Round | Boston | Chicago | Result |
| 1927 | Quarterfinals | Bruins | Black Hawks | Bruins 10-5 (two-game most-goals series) |
| 1942 | Quarterfinals | Bruins | Black Hawks | Bruins 2-1 |
| 1970 | Semifinals | Bruins | Black Hawks | Bruins 4-0 |
| 1974 | Semifinals | Bruins | Black Hawks | Bruins 4-2 |
| 1975 | Preliminary | Bruins | Black Hawks | Black Hawks 2-1 |
| 1978 | Quarterfinals | Bruins | Black Hawks | Bruins 4-0 |
| NBA | ||||
| Year | Round | Boston | Chicago | Result |
| 1948 | Quarterfinals | Celtics | Stags | Stags 2-1 |
| 1981 | Conference Semis | Celtics | Bulls | Celtics 4-0 |
| 1986 | First | Celtics | Bulls | Celtics 3-0 |
| 1987 | First | Celtics | Bulls | Celtics 3-0 |
| 2009 | First | Celtics | Bulls | Celtics 4-3 |
| MLB | ||||
| Year | Round | Boston | Chicago | Result |
| 1918 | World Series | Red Sox | Cubs | Red Sox 4-2 |
| 2005 | ALDS | Red Sox | White Sox | White Sox 3-0 |
| NFL | ||||
| Year | Round | Boston | Chicago | Result |
| 1985 | Super Bowl XX | Patriots | Bears | Bears 46-10 |
The pair of Original Six teams haven't played each other since 1978, but the Bruins have dominated the series history that consists mostly of Bobby Orr-Phil Esposito/Stan Mikita-Tony Esposito battles from the 1970's. The first entry on the list shows the quirky way that the NHL played its opening rounds prior to 1937. Division winners recieved a bye to the semis while the 2-seed and 3-seed in each division would play a two-game most-total-goals-wins set that winnowed the field to four.
* I'll also mention one Chicago-Boston meeting from the old days of the World Hockey Association. The New England Whalers played in Boston during their first two seasons before moving to Hartford and eventually merging into the NHL. After the Whale took the first WHA title in 1973 and won the '74 East Division crown, the Chicago Cougars upset them 4-3 in the first round of the playoffs.
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Other than the bygone days of the Chicago Stags, the NBA's Sam Adams-Old Style rivalry has been rather one-sided. The Celtics swept three series between 1981 and 1987. One of the 11 games was one of the greatest ever played. Game Two of the 1986 series at the Boston Garden featured a young Michael Jordan taking on the great '86 Celtics team that was 40-1 at home in the regular season. Jordan had only played 18 games in his second season due to a broken foot, but he came back for the playoffs and minted the first piece of his incredible NBA legacy.
MJ scored a playoff-record 63 points, but was done in by the more complete team and Larry Bird's 36-12-8 line and Kevin McHale's 27 points and 15 boards. After the game, Bird said "I think it's God disguised as Michael Jordan."
2009 brought an epic seven-game first-round clash. Three of the first five games went to overtime, but it was Game Six that put the series among the all-time best. The reigning-champion Celtics led 3-2, but the Bulls forced Game Seven with a 128-127 triple-overtime win.
Back in Boston, the Celtics won 109-99 to take a series that set NBA records for overtime games (four) and overtime periods (seven).
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World War I forced the 1918 baseball season to end early and the World Series was played in September. The soon-to-be star-crossed Cubs and Red Sox had won six of the first 14 World Series and the 15th would be a low-scoring affair.
In Game One at Comiskey Park (Chicago's games were held on the South Side because the park was bigger than Wrigley Field), southpaw Babe Ruth tossed a six-hit shutout to put the Red Sox in front. The next two games in Chicago (wartime travel restrictions made for an unusual 3-4 home-field format) were split.
The fourth game really swung the series. Although the Cubs scored twice off Ruth in the top of the eighth to tie it 2-2, a sac bunt and errant throw to first in the bottom half gave Boston a 3-2 victory and 3-1 lead.
Chicago staved off elimination with a Hippo Vaughn five-hit shutout in Game Five, but the Red Sox put it away the next day with a 2-1 win. Despite only scoring nine runs in six games, Boston took the title. It's the last (and probably forever will be the last) World Series in which nobody hit a home run.
The champion Red Sox moved to 5-0 during the first 15 Fall Classics. They would somewhat famously go without another title for another 86 years. The Cubs' championship drought reached ten years and it's still going. And going. And going.
There wouldn't be a Cheers-Family Matters matchup in the playoffs until 2005, when the Red Sox and White Sox played in the ALDS.
Chicago rolled to a 14-2 victory in the opener before digging out of a quick 4-0 hole in Game Two to win 5-4 and head to Boston up two games to none.
In the third game, the Pale Hose were clinging to a 4-3 lead in the sixth, but Boston had the bases loaded with nobody out. Orlando Hernandez came out of the bullpen and saved the day, getting two pop outs and a strikeout to preserve the lead. El Duque posted two more zeroes before handing the game to closer Bobby Jenks, who set down the Red Sox 1-2-3 to finish the sweep en route to the South Siders' first championship since 1917.
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We end with the one Will Hunting-Ferris Bueller matchup from the NFL.
The 1985 New England Patriots became the first team to win three road games and reach the Super Bowl in New Orleans*.
* The Pats were the only team to do it until 2005, but now it's happened four times in the last eight years. Not only did the 2005 Steelers, 2007 Giants, 2010 Packers and 2012 Ravens all win three road games in the playoffs, they all won the Super Bowl as well.
Meanwhile, the powerhouse Bears went 15-1 and shut out the Giants (21-0) and Rams (24-0) in their two playoff games to win the NFC.
The 10-point underdog Pats actually took the lead 89 seconds into the game after a field goal followed a Chicago fumble. But it quickly turned into one of the most lopsided Super Bowl blowouts ever. Chicago's menacing defense keyed a run in which the Bears forced five turnovers and scored 44 straight points. New England scored a touchdown in the fourth quarter, but the Bears added another interception and a safety to shuffle their way to a 46-10 win.
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