in Hull's next league game, as they lost 5–0 to Wigan, for Windass' first Premier League game since leaving Middlesbrough. It was his only action during Hull's start to the season, which saw them take 14 points from their first seven games, leading to Windass being frustrated at his lack of first-team action. After he was left out of the squad to face Everton on 21 September 2008, he held talks with manager Phil Brown, following which he vowed to stay and fight for his place. Because he was out of the side, his former club Bradford City, now in League Two, and League One club Leeds United both made bids to sign Windass. In the early hours of 12 November, Windass and teammate Marlon King fought in a casino in Scarborough, with King reported to have headbutted Windass. In the following days, the club said the argument had been settled internally and both players allowed to stay with Hull. Windass had to wait till 22 November 2008 to make another Premier League appearance for City, coming on as a substitute against Portsmouth with Hull trailing 2–1. Windass claimed the goal that earned Hull City a draw, with a header from a corner that deflected off defender Noé Pamarot and into the net. This was officially recorded as an own goal at the time, but was later awarded to Windass after a review by the Dubious Goals Committee. In a radio interview after the game, Windass described the casino incident as a "storm in a teacup". In the following game, Windass was booked for unsportsmanlike conduct without even playing, after he warmed-up too near opposition player Rory Delap while Delap was taking a throw-in. He made his first Premier League start for Hull on 26 December 2008 against Manchester City at the City of Manchester Stadium. Hull lost 5–1, in a game in which they received their half-time team talk from manager Phil Brown on the pitch. Disappointed by his lack of first team opportunities, Windass was allowed to leave Hull, and, on 9 January, he joined Oldham Athletic on loan for the rest of the season. He was expected to make his debut the following day, but had to wait after Oldham's game with Hartlepool United was postponed and re-arranged for two days later. Windass hit the crossbar before he was substituted in the final minute of the game