Gardena Spring Trophy
In 2000, Pennington won both his Junior Grand Prix events and placed 6th at the Junior Grand Prix Final. At Nationals, he won the gold medal on the Junior level, making him the first and so far only man to win Nationals on all of the following levels: Juvenile, Intermediate, Novice, and Junior. Pennington was originally scheduled to compete internationally on the Junior Grand Prix in the 2001–02 season. However, following the September 11, 2001 attacks, the USFSA withdrew all their skaters from the JGP. After placing 13th in his senior-level national debut, he won the junior gold medal at the Gardena Spring Trophy.