[3] He averaged 18.3 points and 4.9 rebounds per game and led Longmont to a 25–2 record, while once again being selected to the all-state first team and named the Northern League Athlete of the Year.

Jessup's play drew comparison to former Boise State player Anthony Drmic.

[6] He averaged 11.6 points per game as the second option behind Chandler Hutchison and hit 46 percent of his three-point attempts.

[11] Jessup made his 276th career three-pointer in a game against UNLV on January 8, 2020, breaking Anthony Drmic's Boise State record.

[12] On February 4, 2020, Jessup broke the Mountain West Conference record for career three-pointers when he passed BYU's Jimmer Fredette's mark of 296.

[18] After playing for the Warriors in the 2022 NBA Summer League, Jessup joined Basket Zaragoza of the Spanish Liga ACB for the 2022–23 season.

[20] On August 10, 2023, Jessup signed with the New Zealand Breakers for the 2023–24 NBL season, returning to the league for a second stint.