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A two-time heavyweight champion, Mike Tyson last held the title in November 1996, two months before his upcoming opponent was born. The 58-year-old legend will face 27-year-old Jake Paul on Friday, November 15 in a matchup between a boxing Hall of Famer and an internet celebrity who gained his fame through YouTube. Paul has worked his way to a 10-1 professional record, last defeating Mike Perry via TKO in July. Tyson hasn't fought professionally since 2005, when he quit on his stool versus Kevin McBride before announcing his retirement afterwards in the ring.

The latest Jake Paul vs. Mike Tyson odds from FanDuel list Paul as the -245 favorite (risk $245 to win $100) to win, with Tyson a +196 underdog. The over/under for total rounds is 5.5, while the fight to go the distance is +172. Paul to win by knockout is +120, while Tyson to win by knockout is +260. The Netflix broadcast starts at 8 p.m. ET. Before making any Mike Tyson vs. Jake Paul picks, make sure you see the boxing predictions and betting advice from SportsLine combat expert Brandon Wise.  

Wise, who is the combat sports editor for CBS Sports, is an experienced boxing and mixed martial arts analyst who has consistently provided winning selections for SportsLine members. For the past four years, he has hit numerous boxing selections in big-time matchups.

For example, in March, Wise called a win in Round 1 for Paul (+200) against Ryan Bourland and also advised SportsLine members to take the Under 1.5 rounds (+120). Both bets connected when Paul scored a knockout towards the end of the first round. Anyone who has followed Wise's combat sports picks on boxing betting sites has already seen massive returns.

Now, with the Paul vs. Tyson fight card approaching, Wise has studied the matchup from every angle and released confident picks for the fight. You can only see his picks and analysis at SportsLine

Mike Tyson vs. Jake Paul predictions  

Wise has analyzed the Jake Paul vs. Mike Tyson bout and is leaning Over 5.5 rounds at -150 odds. While the stamina of a 58-year-old deservedly is a concern, Tyson did manage to go the distance in an eight-round exhibition versus fellow Hall of Fame boxer Roy Jones Jr. in 2020. In his last pro fight in 2005, and even though he admitted his heart wasn't in it, Tyson still went six rounds. Plus, the 14-ounce gloves being used for this fight are much heavier than the standard 10-ounce gloves for heavyweight fights, and that will slow down both fighters' punching power and likely prevent an early knockout.

As for Paul, he's faced mostly MMA fighters or hand-picked novice boxers designed to make him look good, with one exception. Paul took on Tommy Fury, brother of Tyson Fury, in Feb. 2023, and that fight went the distance. Tommy Fury had just eight pro bouts under his belt, while Tyson has 58, and that experience should allow The Baddest Man on the Planet to last until the sixth round, at least, making the Over (-150) the value pick. See who to pick here

How to make Jake Paul vs. Mike Tyson picks

Wise has also locked in a confident money line pick and a method-of-victory prop bet that could pay out big. He's only sharing his picks and analysis at SportsLine.

Who wins Mike Tyson vs. Jake Paul on November 15, and which Paul vs. Tyson props should you be all over? Visit SportsLine now to see Brandon Wise's best bets for the July 20 bout, all from the CBS combat sports specialist who just called Paul's first-round win in March, and find out.