Holzhauer won 32 games, earning $2,642,216. His winning streak lasted from April 4, 2019 to June 3, 2019. During his winning streak, he broke several show records. On April 9, 2019, Holzhauer broke the one-day record with $110,914, breaking the previous record of $77,000 set by Roger Craig in 2010. He breaks his own record with $131,127 on April 17, 2019. He is the first and only player in the show's history to win $100,000 or more in a single game; and he holds the top sixteen spots for most single-day winnings.
On June 3, 2019, Holzhauer lost to a player named Emma Boettcher, who won three games of her own after that. They were both brought back for the Tournament of Champions, which aired November 4-15, 2019. In the tournament, Holzhauer defeated Boettcher in the two-day final, winning the $250,000 prize.
In January 2020, Holzhauer faced off against Ken Jennings and Brad Rutter in Jeopardy! The Greatest of All-Time, finishing in second place with Jennings winning the $1,000,000 first prize and Holzhauer taking home $250,000 for second palce.