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The Bucs return home for the next Homestand against their next division rivals, the Milwaukee Brewers. The Brewers and Pirates first met in a 2 game series on May 26th and 27th in Milwaukee. The Brewers won both games on walk offs 3-2. The Brewers won the next two games, but only ended up winning 6 of the 11 games that year. In 1999, the Brewers would win the first 3 games, but this time would end up winning 8 of the 12 total games they played. There were no walk offs in the year of 1999 between these two teams.

From 2000-2016, the Brewers only made the playoffs twice, in 2008 and 2011. The Pirates didn't make the playoffs until 2013, but than made in 2014 and 2015. However, in the end, neither team was all that successful in this time period. The Brewers won the series in 2000, but than lost the series in 2001, and got dominated in 2002. They fell behind in the series 31-40 after that season. Despite winning the series in 2003, they got dominated in 2004. After a few years of being average, they took control in 2008, winning fourteen of the fifteen games that year. They would have a stretch winning 17 straight games, starting on July 4, 2008, and ending on July 20, 2009. They were dominating the Pirates. The Brewers continued to have success against the Pirates in 2010, winning the overall series and winning games by scores of 17-3 and 20-0. They also won all but three games in 2011, and all but four games in 2012. The Pirates took control the next couple years, but even in 2015 when they made the playoffs, they still lost the series 10-9. The Pirates did win the series in 2016.

In 2016, the Pirates won 10 of the 19 total games. Despite the Brewers making the playoffs in 2018, and nearly making it in 2017, they also won the series in both of those years. They even had a five game winning streak in 2018. But the Brewers still lead the overall series, 186 to 159.