After beginning the following season with his parent club, but without breaking into the first team, he again returned to Sixfields on loan until the end of October. In late 2009, Little went out on loan again, this time for two months at League Two side Chesterfield.
After starting the following season with his parent club but not making it into their first team, he returned to Sixfields on loan until the end of October. Later that year, in late 2009, Little was loaned out again for two months to League Two side Chesterfield.