In his first season as a professional, Frecklington did not initially make the first team squad and in September 2005 he was loaned to Stamford in the Southern League Division One East to gain further experience, remaining until Lincoln recalled him in December 2005. While at Stamford he played alongside his uncle David Frecklington who had been an apprentice at Lincoln City in the mid-1990s. Upon his return to Sincil Bank he became a regular presence on the substitutes bench and on 4 February 2006 stepped off the bench to score his first league goal in the game at Stockport. His reward was his first league start the following week at home to Torquay United. Always impressing, he made 18 league appearances in the second half of the season though only three of these were starts.