[5] Following his leg break, Whelan was sold to Crewe Alexandra, where he made his debut on 23 February 1963 in a 4–0 first round League Cup defeat at Port Vale, and notched up 115 appearances through to April 1966.

In 2005, JJB Sports was fined £5.5 million by the Office of Fair Trading (OFT) for fixing the price of the English National Team and Manchester United shirts in 2000 and 2001.

[9] However, in October 2006, he personally intervened to overturn the settlement of a pay dispute at JJB's Wigan warehouse negotiated by new chairman Tom Knight, branding it "the equivalent of Communism", prompting a two-day strike.

[19] In 2007, he called for the relegation of West Ham United as punishment for their incorrect registration of Carlos Tevez and Javier Mascherano.

It was a dramatic final-day Premiership survival story, with the result saving Wigan and condemning Sheffield United to the Championship.

[22] On 11 May 2013, in a dramatic ending to the FA Cup Final against Manchester City, Ben Watson scored a header in the 91st minute to win the game 1–0.

After the announcement of Maurice Lindsay's intention to retire immediately from the club after the Warriors' loss at the hands of Catalans Dragons on 29 July 2007, Whelan managed to persuade him to stay on until the end of the season.

After the announcement of Lindsay's retirement however, Whelan said he would be willing to sell the club after a proposed takeover from a "genuine Wigan fan" earlier in the year.

[23] On 24 October 2007, it was announced that Ian Lenagan, former owner of Harlequins RL, had completed his takeover of Wigan Warriors, buying out Whelan's 89% stake in the club with the deal taking effect from 1 December 2007.

[28] In November 2014, Whelan was accused of making antisemitic statements, following an interview he gave The Guardian, defending his decision to hire Malky Mackay as manager of Wigan.

Mackay was under investigation by the FA for alleged racism and antisemitism in e-mails and text messages he sent while manager of Cardiff City.

"[29] The statements were condemned by West Ham United co-chairman David Gold and former FA and Premier League executive Simon Johnson, both of whom are Jewish.

[32] Anti-racist organisation Kick It Out offered support to Whelan, saying that they had a responsibility to ensure that people of his age would understand "modern expectations".