In a short show, Joe Ostrowski reacted to the Bears making a quarterback switch from Mitchell Trubisky to Nick Foles in a come-from-behind win against the Falcons on Sunday. Later, Ostrowski previewed the matchups for the White Sox and Cubs in the wild-card round.

Joe Ostrowski opened his show by discussing the Cubs and White Sox continuing to slump with the playoffs nearing. He then listened and reacted to comments from Bulls executive vice president of basketball operations Arturas Karnisovas and new coach Billy Donovan as the organization welcomed Donovan with his introductory media session. It included Donovan sharing his expectations for the Bulls moving forward. Later, Bets Sweats host and executive producer Eli Hershkovich joined the show to discuss the latest trends in sports betting ahead of Week 3 in the NFL.

In the final hour, Joe Ostrowski listened back to some of the best interviews of the day on the station in Score Rewind. He heard from CBS Sports HQ baseball analyst David Samson on his own show earlier in the evening, Fox Sports baseball reporter/analyst Jon Morosi on the McNeil & Parkins Show and Score football expert Hub Arkush on the Dan Bernstein Show. Later, Ostrowski provided an update on his strawberry nightmare.

In the third hour, Joe Ostrowski was joined by Josh Nelson of Sox Machine to discuss the White Sox's decision to stand pat as the trade deadline passed Monday afternoon. Later, Ostrowski listened and reacted to sound from White Sox general manager Rick Hahn and Cubs general manager Jed Hoyer explaining their respective team's approach and decisions at the trade deadline.

In the second hour, Joe Ostrowski was joined by Brett Taylor of Bleacher Nation to discuss the Cubs making a series of low-profile deals ahead of the trade deadline Monday afternoon. What roles will the new additions fill? Later, Bryan Perez of NBC Sports Chicago joined the show to discuss the Bears' ongoing quarterback competition.