Early years

Craig took over the club in as chairman in 1990, taking over from Michael Sinclair, a former businessman who is now a local priest. He enjoyed success under the guidance of manager John Ward and, later, Alan Little, York enjoyed their best period in recent years. The club won promotion to what was then the English Second Division (now League One) in 1993 before making headlines with its giant-killing cup exploits, beating Manchester United over two legs in the League Cup. The cup glory continued the following year. Craig earned national notoriety in 1994 by becoming the only chairman to refuse to sign up to the "Let's Kick Racism Out of Football" campaign.

Latter years; sell off and results

The following years under Craig were bleak for York, with relegation to Division Three and managers coming and going.

In July 1999, Craig wrote to all York City's shareholders, asking them to approve a plan to transfer the club, and Bootham Crescent, to a new company, Bootham Crescent Holdings (BCH). Craig pointed out that he and his three fellow directors, John Quickfall, Colin Webb and the former playing hero Barry Swallow, owned 94 per cent of the shares and had already approved the plan. This sent York into serious financial turmoil, and the club went into administration shortly after Craig had sold it, minus all fixed assets, to John Batchelor for a fee rumoured to be £50.

York City was later rescued by a trust, which had been set up by the club's supporters. Craig sold the ground back to the Supporter's Trust, but for a figure that was many times larger than the reputed £50,000 that he reputedly paid for the club, many years earlier.

In 2002, Douglas Craig was on a 3 man FA panel that overruled The Football League’s decision that had prevented Wimbledon moving to Milton Keynes. On appeal, The Football League allowed Wimbledon to relocate to Milton Keynes in 2003.^[2]