With the NFL season approaching, today's episode focuses on the last-second chaos that's occurred amongst the league. Major contract extensions, sudden injuries, and revisiting past moves were all on the agenda for Episode 3.

The MLB trade deadline is around the corner, leaving Dean and TyGuy with some predictions to make. They also discuss Emmanuel Clase's gambling investigation, more moves in the NBA offseason, and more.

Today, Heading Into Overtime ranks their favorite free agency signings in the NBA offseason. Dean and TyGuy analyze which moves made certain franchises stand out, as well as the teams that failed to achieve their goals.

The guys also dive into MLB All-Star festivities and some interesting moves in the NFL offseason so far.

TyGuy & Dean from Dodgerfilms discuss their podcasting debut, what to expect, and dive into trending topics in sports such as: LeBron's potential last season, Shohei Ohtani back on the mound, and the Madden curse.

Episode 5 of Season 3 covers a lot of the wild upsets we saw in Week 6 of the NFL Season and the MLB playoffs so far. The New York Jets have been impressive, Detroit Lions being discussed as favorites, and QBs may or may not be slightly overrated. The Heading Into Overtime crew discussed how boring the MLB playoffs have been and who will walk away with the World Series trophy. Fun, new topics are brought up this episode.

Coming off of a frustrating loss, Tyler Ferrin vents to co-host Dylan Long about the Dallas Cowboys. MLB Playoffs are finally here, and the Boys recap what we've seen so far in the postseason. Dylan explains his World Series tickets and why he's a winner regardless, while Tyler mentions how dominant this postseason has been by the winning teams. With a lot of time left in the NFL season, Dylan and Tyler discuss how they see certain scenarios playing out. Another episode packed with sports.

Who would've thought the Boys would be talking about Taylor Swift on the podcast? Season 3 Episode 3 dives into the romance between Travis Kelce and Taylor Swift, the Cowboys' tough week, and a recap of Week 3 in the NFL. Talk about "Twitter QBs' comes up, along with impressive outings for the Texans and the Chargers. Dylan ends the episode with his tierlist of the NFL teams heading into Week 4.

The Chargers are struggled, and the Boys are worried about the future of the franchise going forward. The Boys aren't just worried about the Chargers, but the Bengals and Browns are concerning and a conversation needed to be had. This episodes consists of a recap of Week 2 and a preview of the Thursday Night Football matchup, and more.

Season 3 Episode 1 kicks off a new beginning for the Heading Into Overtime Podcast. New members Blake Clay and Taylor Gatto introduce themselves to the audience and express their opinions on NFL Week 2. The crew dives into Aaron Rodgers' injury, the AFC struggles, and the best bets for week 2.

The final episode of Season 2 announces the new members of the Heading Into Overtime Podcast going forward, as long as a preview of the 2023-24 NFL Season. The Boys discuss their favorite teams going into the season, MVPs, Super Bowl picks, and their 6-man PrizePicks NFL season-long parlay.

With the NBA offseason bound to kick off, the Boys go over the trades (Bradley Beal, Chris Paul, Kristaps Porzingis) that occurred over the past few days and the NBA Draft. A City Connect draft is held, as well as the Boys' opinion on Buck Showalter and the Mets.