As a junior at Xavier, he was selected as the 2011 Atlantic 10 Conference player of the year and was named to several All-America teams in the 2010–11 season.

[1] Holloway was a part-time starter as a freshman, then became the starting point guard as a sophomore, playing alongside future NBA player Jordan Crawford.

He was selected as the 2011 Atlantic 10 Conference men's basketball player of the year as he led the Musketeers to another regular-season championship.

[6] In December 2011, Holloway received press for his role during and after the game with rival Cincinnati that ended with a brawl between the teams.

On June 18, 2015, Holloway signed with Mets de Guaynabo of the Puerto Rican Baloncesto Superior Nacional.

[19] On April 8, he returned to Guaros de Lara, making his debut the same day in a win over Gaiteros del Zulia.

[25] On August 11, 2017, Holloway led Piratas de Quebradillas to win the 2017 BSN championship, earning the Finals MVP honors.

[27] On March 17, 2018, Holloway recorded a season-high 28 points, along with 6 rebounds, 5 assists and 3 steals, and led Holon to an 86–81 win over Maccabi Tel Aviv.

[31] On January 3, 2021, he had a 22 points, 10 rebounds, and 11 assists performance against Frutti Extra Bursaspor, which marked his first triple double of his career.