The 2005 team at Freeman saw one of the best performances in team history.
At Spotswood, the team finished in the semifinals of both tournaments, placing higher than 17th for the first time ever. The team would also appear at GSAC, the NAQT Virginia Championship, and Virginia's Cavalier Open, skipping Cavalier Classic due to a Homecoming conflict.
Battle of the Brains and VHSL Scholastic Bowl would be the benchmark events for the Rebels. On TV, the team would win against Steward and Clover Hill, and Dave Porter was named to the All-Star team for the second consecutive year, becoming the first repeat All-Star in the program's history. After the Steward game, which taped on the same day as the Homecoming football game, the team made a surprise appearance at the pep rally, garnering wild cheers from the seniors.
In VHSL play, the Rebels finished second in the Colonial District competition, beating Godwin and advancing to Regionals for the first time. Freeman would then host the Central Region tournament, where history would be made. In the third game of the seven-game round-robin tournament, Freeman beat Maggie Walker by the score of 155-140. Freeman would go on to beat the remainder of its competition, claiming the championship with a 7-0 record. This moment was the first time anyone other than the Governor's School had won the Central Region title. The Rebels would go on to finish fifth in the AAA meet, claiming a school-best 11-3 record in VHSL competition.
As the year ended, the team bid farewell to many players, but the next generation, including George Berry, Thomas Chappell, and Landis William Atkinson IV, joined the team late in the year and would be the foundation of the 2007 team that beat Maggie Walker at Ocean Lakes.
The players who graduated in 2005 were
Underclass players who competed in 2005 were