Holloway was considered one of the top point guard prospects in his high school class playing for St. Patrick, with some of the scouting reports naming him as the best point guard in the nation. He and Mike Bibby were consistently named as the two best point guards of the 1996 class. Selected 3 times in the All-State selection, In 1995 he was amongst the top scorers of the Reebok Big Time Tournament with an average of 26.3 points per game, and he was selected to the Parade All-America Second Team. He averaged 22.5 points, 9.1 assists and 5.8 steals as a senior, for a total of 2,151 points, 727 assists and 540 steals during his time at St. Patrick, and was named to the Parade All-America second team and was also named a McDonald's All-American. In the McDonald's All-American Game of 1996 Holloway was the starting point guard for the East team: he recorded 7 points, 8 assists and 6 steals, receiving the Most Valuable Player award.
College career
After considering offers from California, Duke and Georgia Tech, Holloway accepted the scholarship offered by Seton Hall. He had a very solid freshman season, posting averages of 17.3 points and 6.3 assists per game: he was 5th in the Big East conference in scoring. He was selected for the Big East All-Rookie team and for the All-AAC second team. Despite his good season averages, he decided not to declare for an early entry in the draft and continued his college career. His second season at Seton Hall was slightly worse than his rookie season and, despite leading the Big East in assists per game, he had worse averages in all the other major statistical categories. His junior season was his worst of his college career and all his statistics declined. This was the only season in which he averaged a single digit in points per game. His senior season was his best and he was one of the main players of the Seton Hall team that reached the 2000 NCAA Tournament Sweet Sixteen. He focused more on his 3-point shooting, improving his percentage to 40.3%. For this season, showing a better overall performance, Holloway was named the Big East Most Improved Player in 2000. In 978 total minutes played he was Seton Hall top player in assists per game, and he was second in scoring and rebounding. He scored 27 points in his last game, before an ankle injury ended his season. He finished his career at Seton Hall with 1,588 career points and he became the all-time assist leader, with 681 assists, a record that he still holds as of 2018. In 2012 he was inducted in the Seton Hall Athletics Hall of Fame. He played a total of 3,865 minutes with the Pirates.
College statistics
Sources
Professional career
After his senior season Holloway became automatically eligible for the 2000 NBA draft, but he was not drafted by any of the NBA teams. He was invited to the 2000 Summer League by the New York Knicks and the Washington Wizards. He was drafted in the seventh round of the 2000 USBL Draft by the Long Island Surf. He played professionally for Israeli team Hapoel Holon in 2000–01, averaging 15.5 points and 4 assists in 4 games played. In 2001-2002 he played for the Chicago Skyliners. For the 2002–2003 season he signed for the Chester Jets, and he also played for the London Towers. In 2003 he transferred to Turkey, and signed for İstanbul Teknik Üniversitesi: there he averaged 12.2 points, 2.6 rebounds and 4.4 assists in 19 games played. He also played for Ratiopharm Ulm in 2004–2005. In 2005 he returned in the United States, and signed for the Jersey Express. He also played for Marineros de Puerto Plata in the Dominican Republic, where he ranked second in the Liga Nacional de Baloncesto in assists per game. His last team was the Pennsylvania ValleyDawgs for the 2006–2007 season. During his professional career he played in the Dominican Republic, Germany, Israel, Turkey, United Kingdom and Venezuela, in addition to the United States.
Coaching career
After his retirement from the playing career, Holloway was initially included in the Seton Hall staff, but he then transferred to Iona College in 2007; he spent three seasons there, helping coach Kevin Willard. When Willard became Seton Hall head coach, Holloway followed him as one of his assistant coaches. On April 10, 2018, Holloway was hired by Saint Peter's University as their new head coach.
