Even after Ken Jennings 74 game winning streak on Jeopardy in 2004, it was still rare for a contestant to have a winning streak of 20 or greater games. A winning streak of 20 or greater games wasn't achieved again until 2014 (Julia Collins - 20 games) and then 2019 (James Holzhauer - 32 games).

Since James Holzhauer's winning streak in 2019 in which he pioneered a new strategy of placing large bets on daily doubles and picking random categories on the board, we have seen many more winning streaks greater than 20 games.

2004 - Ken Jennings - 74 games

2014 - Julia Collins - 20 games

2019 - James Holzhauer - 32 games

2021 - Matt Amodio - 38 games

2021-2022 - Amy Schneider - 40 games

2022 - Cris Pannullo - 21 games

As of the creation of this question, no one has won 20 or greater games in 2023. Will we see another winning streak of 20 or greater games before the end of 2024? This question will resolve yes once a player completes a 20 game winning streak. It will resolve no at the end of 2024 if this feat has not been accomplished.