Wednesday night produced an amazing hockey game between the Blackhawks and Bruins. Game 1 of the 2013 Stanley Cup Final set the bar for the rest of this highly anticipated series. Chicago and Boston are two major cities and have passionate sports fans. Their teams don’t often play each other in the playoffs but when they do their have been some classics. Last night’s game inspired me to rank the best Chicago vs. Boston playoff games since January 1986. I ranked five games based on the entertainment of the game, the long term significance and milestones in the game. I also took into account the round where the game occurred with the final round being the most important. There might be a little Chicago bias on the list. Just a little.

1. Chicago Bears 46, New England Patriots 10, January 26, 1986

All the games are up for debate other than this one. Despite the blowout score this is one of the most important games in Chicago sports history. It capped off a season for the best defense in NFL history. If the Bears didn’t lose to the Dolphins in the 1985 regular season, it would’ve been the best team ever. The team not only dominated on the field but represented a hard-working, blue-collar city. If I could go back in time I would want to be alive and remember this season. 

2. Boston Celtics 135, Chicago Bulls 131, 2OT, April 20, 1986

Before the Celtics won another championship they swept the eight-seeded Bulls in three games. The memorable game from that series was Game 2 in Boston. Michael Jordan was only in his second season and missed most of the regular season with a foot injury. He returned in the playoffs and put his name in the record books with a 63-point performance. If a player scored 63 points in a playoff game today, the coverage would be off the wall and social media would be going crazy.

3. Chicago Blackhawks 4, Boston Bruins 3, 3OT, June 13, 2013

At this point in the list you are probably wondering, where are the Bulls/Celtics games from 2009? That was a first round series and what we saw Wednesday was a Stanley Cup final. Two original six teams playing each other in a final for the first time ever. It was also one of the longest games in Stanley Cup final history and was extremely entertaining to watch. Wouldn’t be surprised if another game from this series is deserving of this list in the next two weeks.

4. Chicago Bulls 128, Boston Celtics 127, 3OT, April 30, 2009

This is probably too low on the list because this was one of the most back and forth basketball games I ever watched. The Bulls came into this Game 6, down 3-2 in the series. The Celtics were playing without Kevin Garnett and the Bulls were hampered with Vinny Del Degro as their head coach. Hinrich and Rondo went at each other, Ray Allen couldn’t miss and Joakim Noah made the play of the night.

5. Chicago White Sox 5, Boston Red Sox 3, October 7, 2005

Have to get baseball on this list somewhere. One of the best moments in the White Sox World Series run was Orland Hernandez making a relief appearance in Game 3 with the White Sox up in the series 2-0 of the ALDS. El Duque retired all the batters he faced with the bases loaded, no out and Chicago up 4-3 in the bottom of the sixth inning. The White Sox won to sweep the series and only lost one more time before winning the World Series.

Honorable mentions: Games 1, 2, 4 and 5 of the the 2009 Bulls/Celtics series.

Sad note: If the Cubs and Red Sox took care of business in the league championship series in 2003, there would’ve likely been great games from that series. At the time both teams were in long World Series droughts. What could’ve been.