1997–1998: First meetings

The Brewers and Cubs met for the first official time on June 13, 1997, in interleague play, a 4–2 Brewers victory at Wrigley Field in Chicago.^[12] They met for the first time as division rivals on June 15, 1998, a 6–5 Cubs victory also in Wrigley Field.^[13]

1999–2016: Geographic foes and division races

After battling for the NL Central title in both 2007 and 2008, the teams met at Miller Park for the Brewers' home opener in 2009. During the second game of the series on April 11, the Brewers had the highest attendance in Major League Baseball for the rivalry game.^[14]

During games in Milwaukee, it was sometimes common for there to be many Cubs fans in attendance. This has been largely due to the ticket availability at Miller Park; Wrigley Field has routinely sold out in the past, so it has often been easier and cheaper for Cubs fans to watch games at Miller Park (with Amtrak's Hiawatha Service providing low-cost access between both cities and trains often packed during rivalry games either way^[15][16]), leading Cubs fans to call Miller Park by the derisive nickname of "Wrigley North". During the 2006 season, the Milwaukee Brewers started the "Take Back Miller Park" campaign to regain home field advantage. Since then, the dominating presence of Cubs fans has somewhat dwindled as the Brewers have become more popular with local fans following the sale of the team from Bud Selig to Mark Attanasio. Through the 2007 and 2008 seasons, the rivalry became more intense with both teams battling for the National League Central crown, a prize the Cubs eventually claimed both seasons.^[17] During 2008, the Brewers had a sellout streak going at the start of a mid-July series at home against the Cubs.^[18]

The rivalry was less prominent in the early 2010s, as both teams finished well out of playoff contention in 2010, while in 2011 the Brewers claimed the NL Central title and the Cubs struggled to a 71–91 record.

After the 2011 season ended, former Brewer player, coach and manager Dale Sveum was hired by the Cubs to be their new manager in 2012. The Brewers in 2012, won 13 of 17 games against the Cubs to take the all-time series at 118–117.

2017–Present

In 2017, a surprisingly competitive Brewers team led by young prospects and resurgent veterans challenged the defending World Series champion Cubs for the division, the two played in a key end of the season series which led to the Cubs clinching their second division crown in a row, finishing the season 92–70, six games ahead of the 86–76 Brewers.

The rivalry reached a pivotal stage in 2018. After narrowly missing the playoffs in 2017, the Brewers made several acquisitions during the off-season. They signed free agent outfielder Lorenzo Cain and acquired former Miami Marlins outfielder Christian Yelich in a blockbuster trade.^[19][20] These acquisitions, both occurring on January 25, 2018, helped the Brewers match the Cubs in terms of offensive prowess. During the regular season, the Cubs won eight of first nine meetings, but the Brewers ended up winning the last four series against the Cubs and both teams were tied for first place in the NL Central after 162 games. The teams faced off in a tie-breaker game for the division title. Milwaukee won 3–1, winning the division and securing home-field advantage throughout the National League playoffs.^[21] The Brewers also enjoyed a large contingent of Brewers fans at Wrigley Field during this game, which marked a turn in a series where Cubs fans normally "took over" Miller Park.^[22] The Cubs were relegated to the Wild Card Game, which they lost to the Colorado Rockies. The Brewers went on to beat the Rockies in the NLDS but lost to the Los Angeles Dodgers in the NLCS. The two would remain competitive in 2019 & 2020, with the Brewers making the playoffs in 2019 as a wild card and the Cubs winning the division in the Pandemic shortened 2020 season (the Brewers would make the playoffs as a wild card that year). However it cooled off for a few years following the Cubs sell off of their 2016 World Series core leading to two under .500 seasons, while the Brewers won the division in 2021 and narrowly missed the playoffs in 2022, however never made it past the first round. In 2023, the rivalry came back when this time a young Cubs team led by prospects and resurgent veterans (led by free agent signings Cody Bellinger, Dansby Swanson and Marcus Stroman) challenged a first place Brewers team for the division. The Brewers would win the division, the Cubs would collapse and miss the playoffs, the Brewers would once again be knocked out in the first round.