Matt begins the second hour on how long the Twins and Red Sox game was last night and how it went into 17 innings. Matt then talks on how he would like to put a "Sudden Death" rule in and make extra innings more quicker. He then closes the second hour with an interview talking about the man who won 100,00 USD on The St Louis Blues winning the Stanley Cup.

Matt begins the show talking about the Memphis and Utah NBA trade and then hops into a conversation about the Al Horford and Kyrie Irving situation in Boston and closes the first hour with an interview.

Matt starts the third hour covering the Rockets, many peoples' top choice for the NBA championships in the 2019-2020 season, and their key players Chris Paul and James Harden. Are there chemistry issues between Paul and Harden? How will the Rockets overcome it? Is there a trade for Chris Paul on the table? Cody Stoots of Houston's sportsmap.com joins Matt on the show to further go into the tensions in the Rockets roster from a native perspective. To finish the final hour of the show, Matt encourages fans to engage with the show on social media and goes over the NBA draft one last time.

Matt begins the second hour of Pushing the Odds discussing professional sports gambling and whether or not the state of New York will legalize mobile gaming in time for football season. He is joined by Casey Clark of the American Gaming Association, dives into the topic with further detail, and discusses the potential future of sports gambling in the US. Later in the hour, Matt continues the ongoing discussion about free agency and trades in the NBA, focusing on recently-released free agent Harrison Barnes. Chris Forsberg joins Matt on the show to discuss the future for Kyrie Irving and how the Celtics factor in. Matt finishes the hour talking about Vanderbilt point guard Darius Garland and his potential outcomes from the draft.

Matt starts off Hour 1 talking all things NBA draft: who the first three picks will be and Boston trying to make moves going up in the draft. Matt then goes into the Hard Four segment discussing LaVar Ball's future television appearances being affected by a recent inappropriate comment and other hot topics. He mentions the Toronto Raptors' championship parade again later in the hour, tying it into Kawhi Leonard's undetermined future, as the city of Toronto and the Prime Minister of Canada made it clear yesterday that they want Kawhi to stay during the parade. Matt is joined by Paul Jones of Raptors Radio (@Paul__Jones on Twitter) to discuss Kawhi's future. He finishes the hour reporting on the hunt for missing person and former Panthers running back Rod Smart.