[4] He attended Staples High School in Westport, where playing basketball as a junior he was second team All-Conference and Connecticut Post Honorable Mention.

He was named UAA Player of the Year, First Team All-UAA, and National Association of Basketball Coaches (NABC) All-American.

[11] He returned to Palma for the 2014–15 season, after helping the club earn a league promotion to the LEB Oro (Spanish 2nd Division).

DiBartolomeo, who made 5/7 shots from 3-point territory, was elected co-MVP of the game, alongside his teammate Gregory Vargas.

[16] On December 25, 2016, DiBartolomeo recorded a career-high 35 points, shooting 11-of-14 from the field, along with 7 rebounds and 5 steals in a 93–85 win over Hapoel Eilat.

Despite falling short to Hapoel Jerusalem in the title game, DiBartolomeo was named Israeli League MVP for the 2016–17 season.

[20] On October 5, 2017, DiBartolomeo led Maccabi to win the 2017 Israeli League Cup by averaging 15.3 points, 5 assists, 1.6 rebounds and 1.6 steals per game.

On October 22, 2018, DiBartolomeo recorded a season-high 22 points, shooting 6-of-13 from the field, along with seven rebounds and two assists in a 66–64 win over Hapoel Be'er Sheva.

[25] On November 1, 2018, DiBartolomeo was named Israeli League Player of the Month after averaging 17.3 points, 4.8 rebounds, 2.8 assists and 1.5 steals in four games played in October.

[27] On November 7, 2019, DiBartolomeo recorded a EuroLeague career-high 19 points, shooting 6-of-8 from the field, along with three steals in a 104–78 win over Alba Berlin.

[28] On December 5, 2019, DiBartolomeo was ruled out for six months after he suffered from a pectoral muscle tear in a game against Bayern Munich.