The fortieth episode of Will's Fifth Quarter Special features the host Will Farlow and a guest appearance from, Steve Wrzala. The first segment features Will Farlow opening with his thoughts of the Chicago Bears to this point in 2019. The Chicago Bears lost Week 5 in London in a close loss to the Oakland Raiders, and Steve helps Will dissect the Week 5 loss and its impact on the Monsters of the Midway moving forward in the 2019 season. The Bears had a bye week during Week 6 and Will shares his view of the bye week and how it can help the Bears bounce back in Week 7. The Chicago Bears host the New Orleans Saints Sunday afternoon in a good Week 7 matchup and Will explains the things the Bears need to fix and watch for on Sunday. Chicago Bears QB Mitchell Trubisky returns for this Week 7 game Sunday facing questions of him as the Bears starting QB moving forward, and Steve feels the jury is still out on Mitch Trubisky and his future with the Chicago Bears. Host Will Farlow concludes the segment by giving his predictions for the Week 7 home matchup where the Chicago Bears host the New Orleans Saints Sunday afternoon. The final segment closing the show is Will's Sports Movie Moment where Will shares a sports movie moment favorite in a segment where the host and guest co-hosts share a favorite moment in a sports movie favorite comparing it to a moment in modern-day sports.