As head coach of Seton Hall, he led the top-seeded Pirates to the 2024 National Invitation Tournament (NIT) championship.
He averaged 22.5 points, 9.1 assists and 5.8 steals as a senior,[9] for a total of 2,151 points, 727 assists and 540 steals during his time at St. Patrick,[10] and was named to the Parade All-America second team (for the second year in a row) and was also named a McDonald's All-American.
[17] During his freshman year, Holloway posting averages of 17.3 points and 6.3 assists per game and was 5th in the Big East conference in scoring.
[18] His senior season was his best and he was one of the main players on the Seton Hall team that reached the 2000 NCAA tournament Sweet Sixteen.
[19] In the 2000 NCAA Tournament, he scored 27 points, including the winning basket with 1.9 seconds left in overtime, in the Pirates 72–71 first-round victory over seventh-seeded Oregon.
In the next game against second-seeded Temple, Holloway suffered an ankle injury on a successful fastbreak drive for a layup, ending his season.
[28][29][30] In 2003 he transferred to Turkey, and signed with İstanbul Teknik Üniversitesi: there he averaged 12.2 points, 2.6 rebounds and 4.4 assists in 19 games played.
[35] Instead of continuing his playing career in Germany, Holloway returned to New Jersey and took a position as a substitute teacher and assistant coach at Bloomfield Tech High School.
Just months after moving to Iona, Gonzalez had an opening for an assistant coach and asked Holloway to return to the Pirates.
[37] On March 17, 2022, Holloway led his team to an upset overtime victory in the NCAA tournament over the second seeded Kentucky Wildcats.
15 seed to advance to the Elite 8 in NCAA tournament history, where their Cinderella run ended with a 49–69 loss to No.
[39][40] On April 4, 2024, Holloway's Pirates won the National Invitation Tournament, beating Indiana State 79-77 at Hinkle Fieldhouse.