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Cubs: Top 5 Games to Re-Watch

Looking for classic Cubs games to watch? The Chicago Dugout has you covered!

As we all continue to endure the monotony of life in the midst of self-quarantining, it takes a special motivation to allow creativity to overcome boredom. With Illinois continuing under a ‘Stay at Home’ ordinance until at least May, this reality strikes especially true for those living in Chicago or the ‘burbs.

To that end Major League Baseball threw us all a bone last month, releasing five classic games for every big-league franchise. These games have been made available to stream for free on YouTube, which is a terrific way to escape from reality and revisit some of the Cubs or White Sox great moments, or even to watch amazing moments in baseball history that you may never have before seen.

While the idea itself is brilliant, its execution — at least as much as it concerns the Cubs or the Sox — is lacking, at best. The MLB Vault has several other classic games you can watch, but filtering through is rather tedious.

Here at Chicago Dugout, we’ve taken the liberty to amend MLB’s proposed list for each Chicago team — along with links to stream our picks. First, here’s a refresher of each game MLB selected for the Cubs, coupled with their description for each game:

Arrieta’s masterpiece (Oct. 7, 2015, NL Wild Card Game): Continuing one of the most dominant second halves of a season by any pitcher in history, Jake Arrieta strikes out 11 Pirates and walks none in a complete-game shutout.

Schwarber goes way deep (Oct. 13, 2015, NLDS Game 4): Kyle Schwarber launches a baseball that lands atop the scoreboard as the Cubs beat the rival Cardinals and clinch a postseason series for the first time at home in Wrigley Field history.

Cubs win the pennant (Oct. 22, 2016, NLCS Game 5): Willson Contreras and Anthony Rizzo go deep off Dodgers ace Clayton Kershaw, and Kyle Hendricks shuts down the Dodgers as the Cubs clinch their first pennant since 1945.

They finally win it all (Nov. 2, 2016, World Series Game 7): The Cubs win in extra innings on the road to clinch the team’s first World Series title since 1908, in a series they trailed three games to one entering Game 5.

Bote’s ultimate slam (Aug. 12, 2018): With the whole country watching on Sunday Night Baseball, infielder David Bote comes off the bench and lifts a two-out, two-strike, walk-off grand slam to send Wrigley into a frenzy.


While the selections for the Cubs isn’t altogether terrible, there’s too much recency bias. Every game selected comes within the four year playoff run of 2015-19.

The main rule is this: any game selected for the Cubs or the Sox must not be a repeat of the MLB list above.

Our attempt was to select games that remain iconic and also occurred within our lifetimes — or at least feature players that impacted our childhood fandom. We also took pains to vary games. For instance, the Kerry Wood 20-strikeout game has been omitted as it has received a ton of popularity lately, especially from ESPN’s re-airing it on “Strikeout Saturday”.

Below is our curated list of classic Cubs games to stream. To the best of our ability, each game comes with a link to stream the game for free.

Cubs Defeat Giants in Game 163, Clinch Wild Card Berth (September 28, 1998): The Cubs edged the Giants 5-3 to secure their first playoff berth in nearly a decade. Veteran starter Steve Trachsel struggled with control but turned in 6.1 scoreless innings. Journeyman Gary Gaetti hit a clutch two run homer into the bleachers in the fifth inning that proved to be the game winner. A ninth inning rally by the Giants was quelled by Rod Beck, notching save number 51 and securing the Wild Card at Wrigley Field.

Aramis Ramirez Powers Cubs past Milwaukee (June 29, 2007): Aramis Ramirez caps the Cubs’ comeback in the bottom of the ninth with a walk-off home run. This game extended the Cubs winning streak to seven games, brought them back to .500 (39-39), and ignited the push for their first division title since 2003.

Wood’s Gem Punches Ticket to NLCS (October 5, 2003, NLDS Game 5): Wood outduels Mike Hampton, scattering five hits over eight innings with seven strikeouts and yielding just one earned run. The clutch performance on the road in Atlanta pushed the Cubs to their first NLCS since 1989.

Click for: Innings 2-3; Innings 4-5; Innings 6-7; Innings 8-9

Kyle Hendricks Throws 81-pitch Complete Game Shutout Against the Cardinals (May 3, 2019): Hendricks performs his best Maddux impersonation, scattering four hits, striking out three and surrendering zero free passes while mowing down the Cardinals lineup.

The Ryne Sandberg Game (June 23, 1984): Sandberg bursts onto the scene with two clutch home runs against HOF’er Bruce Sutter, punctuating his MVP season and creating a lifelong relationship with the Cubs’ faithful.


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