In February 1995, local millionaire and owner of JJB Sports Dave Whelan purchased the club, which was then playing in the Third Division (fourth tier), and set out his ambition to reach the Premier League, a statement which was widely ridiculed at the time.Just ten years later, Wigan Athletic were playing Premier League football.
At the end of Whelan's first season as Chairman, Wigan Athletic finished in 14th position in the old Third Division, the 84th rung of the 92-club English Football League ladder. Whelan and Wigan Athletic made headlines in summer 1995 when Whelan's business connections in Spain helped him attract three Spaniards to the club – Roberto Martínez, Isidro Diaz, and Jesus Seba – who became known as 'The Three Amigos'.Martínez and Díaz would later become the first Spaniards to play in the FA Cup, and the trio became the on-pitch symbols of Whelan's ambitious plans.
'The Three Amigos' were joined at the club by John Deehan, who replaced Graham Barrow as manager during the 1995/96 season following a 6–2 home defeat to Mansfield Town. Deehan had coached Norwich City to an unexpected 3rd place finish in the inaugural Premier League season, and his influence took the Latics within two points of a play-off place in his first season. The following year saw the first step towards Whelan's dream come true, when Wigan Athletic became Division Three champions on the last day of the season, in no small part helped by Graeme Jones' club record 31 league goals for the season. Following a mid-table finish in Division Two the following season, Deehan quit to become Steve Bruce's assistant at Sheffield United. He was succeeded by Ray Mathias, who returned for his third stint as Wigan Athletic manager. Mathias' team won Wigan Athletic's second trophy under Dave Whelan, when the Latics beat Millwall 1–0 to win the AutoWindscreens Shield at Wembley in April 1999. More significantly, he took Wigan Athletic to the Division Two play-offs in 1999, losing 2–1 on aggregate to neighbours Manchester City. This ultimately cost Mathias his job as he fell victim to Whelan's relentless drive for Premier League football.
His replacement John Benson led the squad that he inherited from Mathias to a commanding position at the top of Division Two in his first six months, including the demolition of local rivals Preston North End 4–1 away, only to collapse in the second half of the season. This was largely attributed to the dropping of leading goalscorer Stuart Barlow who was responsible for much of the side's early success, coupled with a series of poor quality signings of ageing, and reputedly highly paid players and a run of poor performances led to strong disapproval of the management among fans. The 1999/2000 season ended in failure at Wembley as Wigan Athletic lost 3–2 after extra time to Gillingham at the last ever Division Two play-off final to be played at the old Wembley Stadium.
Benson moved 'upstairs' to the new post of Director of Football in the summer of 2000, when former Arsenal manager Bruce Rioch took the manager's job for the 2000/01 season. Rioch was hampered by severe injury problems and after a difficult and often unimpressive first half of the season left the club in February 2001. He was temporarily replaced by club stalwart Colin Greenall, before the surprise appointment of Steve Bruce for the final eight games of the season. His arrival brought renewed vigour to Wigan Athletic performances, but the club ultimately lost in the play-offs once again, this time against Reading. Following this blow, Bruce left for Crystal Palace after repeatedly pledging his future to Wigan, leaving behind a club both grateful for his help in getting so close to promotion and also angry and bitter at his betrayal.
In the summer of 2001, highly regarded young manager and former Latics forward Paul Jewell took over as manager following an unsuccessful spell at Sheffield Wednesday. His first season in charge saw mixed results and an embarrassing defeat to non-league Canvey Island in the FA Cup first round, although the club eventually finished in mid-table. Jewell's second season in charge was far more successful. Wigan Athletic went on a run to the quarter finals of the League Cup, beating Premier League opponents West Brom, Manchester City and Fulham en route. Wigan Athletic won the Division Two championship in 2002–03 with a points total of 100, powered by the goals of then-record £1.2 million signing Nathan Ellington, with a run of 10 consecutive wins along the way. The club lost only four times all season, and Wigan Athletic secured promotion to the second tier of the English Football League for the first time in their history.
After losing their first ever game in Division One, Wigan Athletic confounded expectations to go unbeaten for the next 17 games and sit atop the division by November 2003. A weak finish saw Wigan Athletic win only three of their last 10 games to finish seventh in Division One – a last minute goal by West Ham's Brian Deane in the final game of the season saw the Latics drop out of the play-off places in favour of eventual play-off winners Crystal Palace.
Hoping to build on the previous season's disappointing finish, the Latics went one better than 2003/04 by remain unbeaten for the first 17 games of the 2004/05 season. Along with Sunderland and Ipswich, the Latics remained in the promotion hunt all season. By the last day of the season, Sunderland had already won the title and Wigan Athletic needed at least a draw against Reading – who themselves needed to win to finish in the last play-off spot – to beat Ipswich to automatic promotion. A 3–1 victory in front of their home fans at the JJB Stadium earned Wigan Athletic promotion to the top division of the English football league system for the first time in their 73-year history.
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