Draftkings NFL Showdown Picks: Cowboys vs. Bears 9/21/25
Dallas Cowboys vs. Chicago Bears
September 21, 2025 4:25 pm EDT
The NFL presents Draftkings football fans with a regular season matchup featuring the Dallas Cowboys and the Chicago Bears. Let’s take a look at this game from a DFS perspective.
Before we dive into the Dallas Cowboys vs. Chicago Bears game let’s review the rules for the Draftkings 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 week’s Cowboys vs. Bears matchup.
Draftkings NFL Showdown Picks
Captain-Dak Prescott, Quarterback, Dallas Cowboys $10,000
Talented quarterback Dak Prescott has certainly been a standout performer for the Dallas Cowboys in 2025. With that said, how has Prescott performed from a data perspective this season? Let’s review the veteran signal caller’s relevant key player game data from the 2025 NFL regular season to answer that question.
In the two games that quarterback Dak Prescott has played for the Dallas Cowboys in the 2025 NFL regular season, Prescott has amassed 549 passing yards, two passing touchdowns and 20 rushing yards.
More recently, in the Dallas Cowboys thrilling 40-37 win over the New York Giants last week, Dallas quarterback Dak Prescott played exceptionally well. Let me be more specific. In the Cowboys victory over the Giants, Prescott tallied a massive 361 passing yards, two passing touchdowns and 17 rushing yards.
I also like Dak Prescott’s matchup in this game. Why? Upon the completion of two games played in the 2025 NFL regular season, in relation to the other 31 teams in the league, the Chicago Bears rank an abysmal 23rd in total passing yards allowed to the quarterback position a game.
As I noted in the rules section above, selecting the correct player at the captain position for a Draftkings NFL Football showdown lineup is absolutely vital if you hope to win a large field GPP (guaranteed prize pool) DFS contest. Keep that in mind as you construct your lineups.
In my view, Dak Prescott is the most likely player to post the most Draftkings points in this NFL regular season game. For that specific reason, I am backing Dallas Cowboys quarterback Dak Prescott at the captain position for this one game NFL DFS slate.
Flex Plays
Jake Ferguson, Tight End, Dallas Cowboys $6,400
In addition to Dak Prescott, tight end Jake Ferguson has been a key contributor for the Dallas Cowboys this season.
In the two games that Jake Ferguson has played for the Cowboys this season, Dallas quarterback Dak Prescott has targeted Ferguson 18 times. In those 18 targets just noted, Ferguson compiled 14 receptions and 101 receiving yards.
Flex plays I like to play well in this NFL regular season contest (Draftkings price noted): Caleb Williams, Quarterback (Chicago Bears) $9,600: Javonte Williams, Running Back (Dallas Cowboys) $9,200: Rome Odunze, Wide Receiver (Chicago Bears) $8,400.
