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Cubtober: 10 of the best Cubs playoff moments

October 17, 2025 by WGN 9

CHICAGO — Move over Halloween, the Cubs are back in the playoffs for the first time in five years and fans hope October turns into Cubtober.

With the club looking to march past the Padres in the Wild Card to set up a marquee divisional matchup with Milwaukee, let’s take a look at some of the best moments in Cubs’ playoff history.

Whether it’s a specific moment or an inning or game, here’s 10 of the best.

Cubs comeback in Game 4 of 2016 NLDS

San Francisco’s ace Madison Bumgarner was waiting in the wings for Game 5 of the 2016 NLDS back at Wrigley Field and things were bleak heading into 9th inning of Game 4.

Down three runs, KB singled, Rizzo walked and then Ben Zobrist punched a ball down the right field line.

Just kids at the time, Wilson Contreras and Javy Baez tied and put the Cubs ahead with clutch singles up the middle. The club went on to win 6-5 to set up a showdown with the Dodgers in the NLCS.

Watch moment

SAN FRANCISCO, CA – OCTOBER 11: The Chicago Cubs celebrate after defeating the San Francisco Giants 6-5 in Game Four of their National League Division Series to advance to the National League Championship Series at AT&T Park on October 11, 2016 in San Francisco, California. (Photo by Ezra Shaw/Getty Images)

Baez homers off Lackey in 2015 NLDS against Cardinals

Wrigley was absolutely shaking after Baez hit a three-run home run off John Lackey in Game 4 of the 2015 NLDS. As the broadcast noted, it wasn’t a bad pitch — Javy just extended in only a way “El Mago” could.

Joining in chanting “Lackey, Lackey” directly after was a religious experience. People forget that after allowing two runs in the first, Cubs starter Jason Hammel hit an RBI single up the middle with two outs to set up the homer.

Watch moment

The Chicago Cubs’ Javier Baez (9) rounds the bases after hitting a three-run home run in the second inning against the St. Louis Cardinals during Game 4 of the NLDS at Wrigley Field in Chicago on Tuesday, Oct. 13, 2015. (Brian Cassella/Chicago Tribune/Tribune News Service via Getty Images)

Schwarber goes off the scoreboard, 2015 Game 4 NLDS

Flash forward five innings and one of the most iconic homers in Wrigley Field history happened.

Kyle Schwarber launched a bomb in the bottom of the 7th hit the top of the newly-installed right field scoreboard off the Cardinals.

The ball was encased at the top and the Cubs went on the win 6-4.

Watch moment

CHICAGO, IL – OCTOBER 13: Kyle Schwarber #12 of the Chicago Cubs celebrates at the dugout after hitting a solo home run in the seventh inning against the St. Louis Cardinals during game four of the National League Division Series at Wrigley Field on October 13, 2015 in Chicago, Illinois. (Photo by David Banks/Getty Images)

Cubs beat Kershaw to win 2016 pennant at home

The energy walking to the ballpark was electric on a warm late October afternoon in 2016.

The Cubs had one of the best pitchers ever, Clayton Kershaw, in their way. “Kershaw, Kershaw” chants erupted from the bleachers when he was warming up on the field.

A little bit later he was in hell during the first inning, giving up two runs. The Cubs went on to win 5-0, capturing the club’s first pennant since 1945.

Watch moment

CHICAGO, IL – OCTOBER 22: Members of the Chicago Cubs pose for a team photo after defeating the Los Angeles Dodgers in Game 6 of the NLCS at Wrigley Field on Saturday, October 22, 2016 in Chicago, Illinois. (Photo by Alex Trautwig/MLB via Getty Images)

Kerry Wood homers in Game 7 of 2003 NLCS

Alex Gonzalez and Steve Bartman were the villains of the infamous Game 6 collapse, but Game 7 still offered hope.

It was dashed in the first after the Marlins put up three runs on a young Miguel Cabrera home run, but Woody stepped up to the plate in the bottom of the second and unleashed a bomb to the left field bleachers.

Chaos ensued but it was short lived.

Watch moment

CHICAGO – OCTOBER 15: Kerry Wood #34 of the Chicago Cubs hits a three-run home run in the second inning against the Florida Marlins during game seven of the National League Championship Series October 15, 2003 at Wrigley Field in Chicago, Illinois. (Photo by Elsa/Getty Images)

Schwarber hits ball into Allegheny

“Whatever helps keep your hope alive, just know, it doesn’t matter,” Jake Arrieta on Twitter circa Oct. 4, 2015.

Gerrit Cole, 98 wins, it did not matter. The Pirates had no chance to beat the Cubs in the 2015 NL Wild Card game and Kyle Schwarber punched an early exclamation mark by crushing a ball in the third inning into the Allegheny River.


Chicago through the years: Wrigley Field

The Pirates were shut out.

Watch moment

PITTSBURGH, PA – OCTOBER 07: Kyle Schwarber #12 of the Chicago Cubs high fives Kris Bryant #17 of the Chicago Cubs after hitting a two-run home run in the third inning during the National League Wild Card game against the Pittsburgh Pirates at PNC Park on October 7, 2015 in Pittsburgh, Pennsylvania. (Photo by Jared Wickerham/Getty Images)

Cubs dominate Scherzer in 2017 NLDS

The Cubs played with a self-admitted hangover from the World Series win in the first half of 2017. They finally kicked it into gear in the back half and had a chance as great as anyone to repeat.

That year, future hall-of-famer Max Scherzer was at his peak and the Nationals had him pitch in relief in the 5th inning. You may expected him to shut the Cubs down — the opposite happened.

Watch moment

WASHINGTON, DC – OCTOBER 13: Willson Contreras #40 of the Chicago Cubs celebrates next to Bryce Harper #34 of the Washington Nationals after Harper struck out to end Game 5 of the National League Divisional Series at Nationals Park on October 13, 2017 in Washington, DC. The Cubs won the game 9-8 and will advance to the National League Championship Series against the Los Angeles Dodgers.
(Photo by Win McNamee/Getty Images)

Cubs 1984 NLCS Game 1

Ask any Cubs fan of a certain age and they still have a deep distain for Steve Garvey. Prior to that awful series of events in San Diego, the Cubs got off to a great start in Game 1 — completely blowing out the Padres during a day game at Wrigley 13-0.

Even “Big Red” homered, watch below.

Watch moment

Chicago Cubs vs. San Diego Padres during the first game of the National League Championship Series at Wrigley Field, 1060 West Addison Street, Chicago, Illinois. ST-30004286-0236, Chicago Sun-Times collection, Chicago History Museum

Montero’s 2016 NLCS Grand Slam

The anxiety in the stands of Game 1 of the 2016 NLCS was palpable. It was a low scoring game until the Dodgers tied it in the top of the 8th 3-3.

With two outs, backup catcher Miguel Montero stepped to the plate, worked a great at-bat and then launched an absolute missile off Joe Blanton for a grand slam.

Watch moment

CHICAGO, IL – OCTOBER 15: Miguel Montero #47 of the Chicago Cubs hits a grand slam home run in the eighth inning against the Los Angeles Dodgers during game one of the National League Championship Series at Wrigley Field on October 15, 2016 in Chicago, Illinois. (Photo by Jamie Squire/Getty Images)

Cubs win the 2016 World Series

The 2016 World Series win transcended sports and was a cultural event not only for Chicago, but for America. The tears, the pure joy felt by millions, the parade — all of it makes it hard to believe we’re coming up on ten years.

Time for the Cubs to do it again.

Watch moment

CLEVELAND, OH – NOVEMBER 2: Members of the Chicago Cubs celebrate defeating the Cleveland Indians in Game 7 of the 2016 World Series at Progressive Field on Wednesday, November 2, 2016 in Cleveland, Ohio. (Photo by Ron Vesely/MLB via Getty Images)

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