The 2005-2006 Campaign was an eventful one. With four starters returning to the team, the Tornadoes looked to build on the late success from the previous season. Chris Newsome joined the returning starters to give the Tornadoes scoring ability at all 5 positions. Jon Morgan and Colby Heckman were two of the best scorers in the league a year ago, and with experience from Chris Thomas and Jonathan Phelps, the sky seemed to be the limit.

The regular season started and Timberlake saw that they were going to be in for a long series of tough challenges throughout the year. LCA had bolstered their roster to become one of the best teams in the league, Holy Cross was returning 4 key players from last season's state championship team, and the VIC was blessed to have two more recruiting schools in VES and Roanoke Catholic join the league. Timberlake was faced with the toughest schedule it has ever had in the history of its existence. The Tornadoes were thrown into the fire quickly in the Holiday Classic losing two tough games to VES and LCA. Both teams finished ranked in the state in their divisions.

TCS was able to get back on the winning track at the Fuqua Invitational Tournament, where they played perhaps their worst game of the season, and defeated Central Virginia Home School 57-54. The next night, Timberlake came out refocused and took it to the host team Fuqua, defeating them 93-74 to win the tournament. It was the most points scored in a regulation contest since the 1992-1993 season. Though it was a successful weekend, the inconsistency and strikingly different performances on consecutive nights would prove to be a microcosm of the entire season.

TCS would ride the momentum into the LC Christmas tournament where they would reel off two more victories over a few of the local public schools. First they faced William Campbell in what would become a dogfight. Both teams exchanged leads back and forth throughout the contest. TCS opened the game by shutting out the Generals in the entire first quarter. The victory was highlighted by Jon Morgan scoring his 1000th career point in the ballgame. One of the major highlights of the year for Timberlake would come in their next contest. They faced E.C. Glass for the first time in school history. Glass is the largest public school in the area and the only AAA school within the local area. TCS came with one of their best efforts of the season and broke open a close game in the second quarter. They shot with an unbelievable efficiency and at one point in the game led by 26 points. Colby Heckman had a break out game scoring 25 points and the team made 6 of their 9 three-point shot attempts. Timberlake played great defense against Glass and was actually able to fast break on the Hilltoppers due to their scrappy defense. In the end, the Tornadoes walked away with a 67-45 victory and one of the most noteworthy school wins in the program's history.

Timberlake would get a few more quality victories over North Cross and Hargrave Military. The victory over Hargrave came in the middle of a rough week with 3 long road trips to Martinsville, Chatham, and Roanoke in four days. TCS looked fresh and spry as they continually attacked the full court press of Hargrave to produce layup after layup. Jon Morgan had a great night scoring 33 points while Colby Heckman added 22.

Ultimately, Timberlake's greatest games were three contests that they lost. They played LCA, who was first place in the VIC, at home near the end of the season. The Tornadoes took an 9 point lead into halftime and tried their hardest to hang on to their lead, but the physical play of the Bulldogs would eventually get the best of Timberlake. A few weeks earlier, Timberlake played Holy Cross to a near stand still on their home court. After leading through a large part of the game, the Tornadoes were staring at an impending overtime session as the score was tied 53-53 with six seconds left. Holy Cross heaved up an off balance three-pointer as time expired and was bailed out by a more than questionable foul call that gave Holy Cross the victory.

Through the tough schedule and even tougher losses, the State Committee was still able to tell that Timberlake was among the best teams in the state in their division. With a final regular season record of 12-16, the committee still voted TCS as the #7 team in the state which qualified them for the state tournament. This was only the second time in school history that Timberlake made it to the state tournament. As fate would have it, the Tornadoes would be paired with the #2 team in the state, Holy Cross. Timberlake knew it would stand a good chance to pull off the upset, but they would have to play a near perfect game. Playing at Holy Cross, Timberlake entered their 2nd ever state tournament game ready to play. The game carried with it an intensity that the Tornadoes had rarely seen, and the lead was exchanged throughout the contest. Colby Heckman was playing in what would be his final game at TCS and he held nothing back. He scored a career high 26 points in the game and made some spectacular plays. Jon Morgan added 20 points and Timberlake looked more like equals with Holy Cross than underdogs. In the end, the Tornadoes would have the ball trailing by one with 30 seconds left. They swung the ball around and got a decent look at the basket from about 5 feet away. They missed, and had to foul. Holy Cross hit their free throws down the stretch and Timberlake suffered their most painful loss of the season.

Timberlake finished the season on a sad note, but there were many things that were positive to reflect on. The quality wins over William Campbell, EC Glass, North Cross, and Hargrave were great moments in the season. It is hard to look at the season and not wonder what could have been. Never had Timberlake been so close to the State Final Four. They were 30 seconds away from accomplishing something no TCS team had ever accomplished. However, TCS still has plenty to be proud of. They finished 7th in the state which was the highest finish for any Timberlake team. They saw Jon Morgan break 1000 points and later in the year, watched him break the career scoring record of Keith Rogers.