Draftkings MLB Showdown Picks: Brewers vs. Cubs 10/8/25
Milwaukee Brewers vs. Chicago Cubs
October 8, 2025 5:08 pm EDT
Major League Baseball presents Draftkings baseball fans with a National League playoff matchup featuring the Milwaukee Brewers and the Chicago Cubs. Let’s take a look at this MLB game from a DFS perspective.
Before we dive into the Milwaukee Brewers vs. Chicago Cubs game let’s review the rules for the Draftkings MLB single game showdown contest.
Draftkings Single Game Showdown Contest Rules
You have $50,000 to utilize on five players from either team. However, one of those players will be designated as your team captain. The captain accumulates 1.5 times the standard fantasy points. Additionally, the captain is 1.5 times the standard cost of the flex position.
The remaining four players in your lineup will receive the standard fantasy points. Having stated that, it is highly important for you to identify the correct player for your captain position if you hope to win a large field DFS GPP (guaranteed prize pool) showdown contest.
If you have additional questions regarding the rules for the single game showdown contest, I recommend that you check out the Draftkings website for more details.
*I recommend that all readers review the starting lineups for both teams prior to setting your DFS lineup for this one game slate.
Here are my Draftkings picks for this afternoon’s Brewers vs. Cubs matchup.
Draftkings MLB Showdown Picks
Captain-Jameson Taillon, Starting Pitcher, Chicago Cubs $10,800
On Wednesday night, Major League Baseball presents the third game of a five-game National League series featuring the Milwaukee Brewers and the Chicago Cubs.
How are these two teams playing entering this afternoon’s MLB playoff game? The Milwaukee Brewers arrive at the third game of this five-game series with the Chicago Cubs playing good baseball. More specifically, the Brewers have won three of the team’s last four games played in the 2025 MLB season, including a 7-3 win over the Chicago Cubs two days ago.
In direct contrast to the Milwaukee Brewers, the Chicago Cubs are playing below average baseball entering this MLB playoff game. The Cubs have lost three of the team’s last four games played in the 2025 MLB season, including a 9-3 loss to the Milwaukee Brewers four days ago.
Now that we have identified how both of these teams are currently playing let’s shift our focus to this afternoon’s American League playoff game. Starting pitcher Jameson Taillon has certainly been a standout performer for the Chicago Cubs this season. With that said, how has Taillon performed from a statistical standpoint? Let’s review the veteran pitcher’s relevant game data from the 2025 MLB regular season to better shed light on Taillon’s overall contributions to his team.
In 23 starts made in the 2025 MLB regular season, Chicago Cubs starting pitcher Jameson Taillon compiled an 11-7 (win-loss record), a 3.68 ERA (Earned Run Average) and a 1.06 WHIP (Walks and Hits per Inning Pitched) which ranks 12th in MLB. It should also be noted that Taillon amassed 98 strikeouts while allowing 27 walks in 129.2 innings pitched in 2025.
What did we learn from the data just presented? The data clearly illustrates that Jameson Taillon can post a high number of DFS points on any given night. Having stated that, I fully expect that trend to continue in this afternoon’s National League playoff matchup with the Milwaukee Brewers.
In my opinion, Jameson Taillon is the most likely player to post the most Draftkings points in this National League playoff game. For that specific reason, I am backing Chicago Cubs starting pitcher Jameson Taillon at the captain position for this one game MLB DFS slate.
Flex plays I like to play well in this MLB playoff game (Draftkings price noted): Quinn Priester, Starting Pitcher (Milwaukee Brewers) $11,000: Michael Busch, First Baseman (Chicago Cubs) $8,800: Isaac Collins, Outfielder (Milwaukee Brewers) $5,600.
