Season 2003–04 was a disappointment for Hibernian, as the team again finished in the bottom half of the Scottish Premier League, and was knocked out at the first stage of the Scottish Cup. The main highlight of the season was the run to the 2004 Scottish League Cup Final, which Hibs reached by defeating both halves of the Old Firm. This also ended in disappointment, however, as the Final was lost 2–0 to Livingston. A month after that defeat, manager Bobby Williamson was allowed to leave the club to manage Plymouth Argyle.

With the Hibs squad "stretched to its limits" by injuries to Ian Murray, Grant Brebner, Stephen Glass and Yannick Zambernardi, Hibs again struggled in the league. Financial problems meant that the club had sold or released many of its senior players during Bobby Williamson's time in charge, and even Williamson's own long term contract was renegotiated to a shorter term and lower salary. The Hibs board were also apparently willing to allow Plymouth Argyle to take Williamson when made an approach in April 2004. Williamson's assistants, Gerry McCabe and Jim Clark, took charge of the team for the remainder of the season, with Tony Mowbray appointed soon after its conclusion.

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