In October of 2023, the WPIAL and its official bank partner First National Bank created the Financial Trivia Challenge for the league's member schools and their students. The Financial Trivia Challenge is a competition for students across Western Pennsylvania to learn important financial skills, with cash rewards distributed to the highest scores and the schools with the most student participation.

Participants have 90 seconds to answer as many financial-related trivia questions as possible. They can improve upon their score by participating as they'd like, while comparing their results with others across the WPIAL on the leaderboard. The top 20 students with the highest scores take home cash rewards of up to $500, and member schools with the most student participants can win a grant of up to $1,500. In the second year of the challenge, participants could take the quiz up to 30 times, and the cash rewards were increased to a grant of up to $2,000 for member schools with the most participation and a cash reward of up to $600 for the top 10 student scores. There were also rewards of $250 to the three schools with the most participation in the challenge's first two weeks.

A year-by-year list of school and student winners, as well as full recaps of the Financial Trivia Challenge, can be found below.
 

Year	Top Participating School	Student High Score	Recaps
2025	Laurel Highlands	Sydney Sekely (South Park)	Recap
2024	Serra Catholic	Maddox McAllister (Laurel Highlands)	Recap
2023	South Park	Isaac Valenzuela (Beaver)	Recap