Though Osborne captained the team on occasion, a lack of confidence meant that he spent periods out of favour with manager Andy Scott, which necessitated spells away on loan at Conference Premier clubs Oxford United and Eastbourne Borough. Osborne scored the first senior goal of his career in a 1–0 win over Shrewsbury Town on 5 January 2008, when he converted a header from a Ryan Dickson corner. He followed up with four further goals during the 2008–09 season, which included a header in a 2–0 victory over Luton Town on the final day, which crowned Brentford's League Two title-winning season and gave Osborne the first silverware of his career.