Brown was rewarded with a new three-year contract, which he signed on the weekend of Hull City's first ever top-flight match, a 2–1 victory over Fulham on 16 August 2008. On 28 September Brown managed Hull to a 2–1 victory at Arsenal. It was only Arsenal's second-ever defeat at the Emirates Stadium and was described by the Hull press as the greatest victory in the club's history. After a 1–0 victory at bottom of the table Tottenham Hotspur the following weekend, and a 3–0 away victory at the also newly promoted West Bromwich Albion, he was awarded the Manager-of-the-Month award for Hull's performances in September.