(Photo by Dilip Vishwanat/Getty Images)

Almost six years ago to the day the Chicago Cubs won the 10,000th regular season game in franchise history. Chicago is only the second club in MLB history to hit this milestone, the first was the San Francisco Giants during the 2005 season.

Since they debuted in 1876 the franchise has won two world championships, 16 pennants, and made 16 playoff appearances. They are now just eight defeats away from setting another regular season milestone: 10,000 loses.

But who will hand the Cubs the history-making loss? To answer, let’s turn to one of my favorite Bill James’s sabermetric innovations: the log5 formula for estimating the winning percentage when two teams meet. By plugging in the expected win probabilities for the Cubs remaining games then running a simulated season 1,000 times we can get a sense of when the 10,000 loss will occur.

Date Game Probability
Monday, May 12 @STL 22%
Friday, May 9 @ATL 21%
Saturday, May 10 @ATL 21%
Sunday, May 11 @ATL 21%
Tuesday, May 13 @STL 17%
Wednesday, May 14 @STL 9%
Thursday, May 8 @CHW 7%
Wednesday, May 7 @CHW 6%
Thursday, May 15 @STL 6%
Friday, May 16 MIL 4%
Tuesday, May 20 NYY 4%
Wednesday, May 21 NYY 4%
Saturday, May 17 MIL 3%
Sunday, May 18 MIL 3%
Thursday, May 22 @SDP 2%
Friday, May 23 @SDP 2%

The May 12 matchup against St. Louis has the highest chance of being the Cubs 10,000th defeat, followed by sometime during the Atlanta series. The Cubs are 1-2 against the Cardinals this season but have yet to play the Braves.

There is just a slim chance (four percent or less) that loss 10,000 happens at Wrigley Field.