Top 10 Moments in Brewers-Cubs History

[Michael Trzinski]

Image courtesy of Tapping the Keg Sports website

The Milwaukee Brewers started playing the Chicago Cubs in 1997, Milwaukee's last year in the American League. The Cubs won two of three contests in that first season of what would become a strong, sometimes bitter, rivalry. The next year, the Brewers moved over to the National League Central, and over the 28 years since, the Brewers and Cubs have each won the NL Central crown six times. Although each team has had stretches of domination over the other, for the most part, the two squads have been evenly matched. In the overall series since 1997, the Brewers hold a slight 230-226 margin over the Cubbies. This Saturday, the Brewers and Cubs will meet for the first time in a postseason series. 

Over the years, many noteworthy games and moments have come from this rivalry, one of the best in baseball. Brewers fans flock to Wrigley Field, calling it 'Miller Park South.' Likewise, many Cubs partisans make the 90-mile drive north on I-94 and do their best to turn the Brewers' home park into 'Wrigley North.' Sometimes it's all in good fun, but other times, it can get more intense—just like it is on the field. Without further ado, here is my list of 10 'Top Moments' that have occurred during the rivalry, listed chronologically.

June 13, 1997
In the first interleague game ever played at a National League ballpark, the Brewers defeated the Cubs 4-2 behind Jeff D'Amico's eight-inning effort, in which he allowed five hits and two runs to earn his third victory of the young season. José Valentin had a double and a home run and drove in three to lead the Brewers. A crowd of 36,107 attended the initial game of the so-called 'Border War.' The next two games saw even bigger crowds, and even though the Brewers dropped both games, a rivalry had begun.

September 6, 2003
Although the Brewers lost to the Cubs, 8-4, a couple of memorable events occurred. First, the largest crowd in Miller Park history (46,218) showed up, despite the fact that the Brewers were 17 games under .500 and had no chance at making the postseason. Second was the return of Randall Simon, the same one who knocked over the Italian racing sausage by swinging a bat at the runner's suit. Simon had been with the Pirates at the time, but was traded to Chicago in August. During the game, the scoreboard announced that Simon would buy Italian sausages for all 330 fans in Section 112. "I think it was an awesome idea," Simon said of the plan suggested by a Chicago coach. "It was a nice way of saying, 'Thank you and I'm sorry,'" 

September 28, 2008
C.C. Sabathia pitched a complete-game four-hitter, allowing only an unearned run while whiffing seven batters, and Ryan Braun hit a two-run homer in the eighth to break a 1-1 tie as the Brewers went on to a 3-1 win over the Cubs, clinching their first postseason berth since 1982. After the game, Braun said, "It's great for the city. Fans here have been waiting a long time." The Brewers came out on the field after celebrating, watching the Florida-New York game on the scoreboard, along with thousands of fans still in the stands. The Marlins beat the Mets, giving the Brewers a one-game edge over the Metropolitans, sending them to the playoffs.

September 23, 2017
Trailing 2-1 heading into the bottom of the ninth, the Brewers tied the game on a leadoff home run by Orlando Arcia off Cubs closer Wade Davis, sending the game to extras. In the top of the 10th, it was the Cubs who roughed up an enemy reliever, using a walk, a bunt, and an RBI single by Jon Jay off Jeremy Jeffress to put the Cubs up by a run. In the bottom half, Braun doubled with one out before Travis Shaw slammed an oppo shot off Davis into the Brewers bullpen for a 4-3 walk-off win.

"It just feels good to help us win," Shaw said.

June 13, 2018
At the beginning of the game, the wind was blowing out to center field at a gusty 15 mph, but Wrigley Field played more like the wind was blowing in as the only run was scored on a Lorenzo Cain home run in the third inning off Cubs starter Mike Montgomery in a 1-0 pitcher's duel, a rare sight at the 'Friendly Confines.' The Brewers managed four hits, including a pair of safeties by Cain. The Cubs knocked out six hits, led by a single and double by Javier Báez.

September 4, 2018
One day after the Brewers took a 4-3 decision on a walk-off groundout by Christian Yelich against the Cubs, the Brewers ran roughshod over the Cubs in the second game of the series, blowing out their Illinois rivals by an 11-1 score. Before the game, Cubs pitcher Cole Hamels downplayed the rivalry between the two clubs. The Brewers led 3-1 in the sixth inning and exploded for eight runs across the next three innings in a laugher. After the contest, a giant (25' x 15') 'L' flag was unfurled by Brewers fans in left field. The Brewers were three games behind the Cubs in the NL Central, but that would change.

September 10, 2018
Before Josh Hader was the Brewers' closer, he was a pretty darned good middle- and high-leverage guy. He had perhaps his best game at Wrigley Field, with the Brewers leading 3-2 in the seventh inning. In that frame, he struck out David Bote, Addison Russell, and Daniel Murphy on 13 pitches, with all the strikeouts being of the swinging variety. In the eighth, Kris Bryant and Anthony Rizzo each struck out swinging on 1-2 pitches. Báez looked at strike three to end a dominating pitching performance by the long-haired lefty. Jeffress pitched the ninth for his 11th save of the season.  

October 1, 2018
Tied at the top of the NL Central after 162 games, the Cubs and Brewers met for an extra game to decide the winner of the division. The Brewers scored twice in the eighth inning to break a 1-1 tie and took the Central title, their first since 2011. The Brewers went ahead late in the game on RBI singles by Cain and Braun, and Hader pitched the last two innings for the save in the 3-1 final. The Brewers won 17 of 22 games after facing the Cubs early in the month, including eight victories in a row to end the season.

November 6, 2023
In the only 'moment' that didn't occur in a game, the Brewers' managerial dynamic changed when Craig Counsell signed a $40-million contract with the hated Cubs, leaving after nine seasons at the Milwaukee helm. Counsell won 707 games while wearing the blue and gold uniform, 144 more than second-place Phil Garner. Milwaukee appeared in five postseasons during his reign and won three NL Central titles. Upon his return to Uecker Field in 2024, Counsell was booed relentlessly.

July 28-29, 2025
Not exactly a moment, but it was perhaps the point of the 2025 campaign where the Brewers displayed their dominance over the Cubs, winning a pair of games before losing the final contest of the three-game set. The Brewers promptly went on a 14-game winning streak to, for all intents and purposes, win the NL Central crown. Although the Brewers won only two times in the infamous five-game series at Wrigley in mid-August, the Brewers had enough of a lead to edge the Cubs by five games. 

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