in the opening fixture of the 1999–2000 season as Torquay defeated Shrewsbury Town at Gay Meadow. He established himself as a first-team regular and played 50 games in all competitions, scoring a total of five goals, the first of which came in a 2–1 victory against Peterborough United on 19 October 1999. Torquay finished in ninth place in Division Three, just three points outside the play-off places. In July 2000, he signed a new two-year deal with Torquay. However, only two games into the following season, he picked up a stomach tear, which kept him out for the rest of the season. Without Brandon, Torquay could not match their high league position of the previous season, and finished 21st, four points above Barnet who were relegated out of The Football League. He returned from injury in time for the start of the 2001–02 season and once again he became an established member of the team during the start of the campaign. He was dropped from the side for a period of time following an FA Cup defeat to Northampton Town in November 2001, during which he missed an open goal. He returned to the first team in January 2002 and scored on his second game back in the starting eleven as Torquay defeated Bristol Rovers. Two months later, he scored a vital goal in a 2–0 victory over Lincoln City, which helped Torquay to only their second home victory in four months and move them 13 points clear of the relegation zone. Torquay finished the season only two places higher than their previous campaign, but 15 points above relegated Halifax Town. During his disrupted three seasons with Torquay, Brandon amassed 83 appearances with ten goals to his credit, before he moved to Chesterfield in July 2002 on a free transfer. Chesterfield Brandon signed a two-year contract with Division Two side Chesterfield, and made his debut against Queens Park Rangers on the first day of the 2002–03 season. Chesterfield lost the game at Loftus Road 3–1. Brandon's first goal for Chesterfield came a week later when he scored a 12-yard overhead kick to give them a late 2–1 victory over Port Vale. He scored again just ten days later as Chesterfield defeated Northampton Town 4–0. His third goal was another volley during a 1–0 victory over Stockport County. However, he was substituted at half-time, and he did not play for another