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In 2002 Gretna were elected to the Scottish Football League, at the third attempt, following the extinction of Airdrieonians because of financial problems. In 2004-05 they were promoted from Division Three after three seasons, and then won the Division Two and Division One titles in successive seasons, in 2005-06 and 2006-07.

They were also runners-up in the Scottish Cup, having reached the competition final for the first time in their history, after beating Dundee 3-0 in the semi-final on 1 April 2006. This made them the first team from Division 2 to reach the final since a third tier was introduced in the 1975/76 season[1]. They lost to Hearts in the final on penalty kicks, after a 1-1 draw after extra time. This did, however, make them the first team from the third tier of their domestic league to qualify for the UEFA Cup. They qualified since Hearts already had a place in the Champions League. During their seasons of successive promotions they scored an incredible 297 goals with 130 coming in the 2004/05 season and a further 97 coming a season later. The 130 scored in the Third Division was 1 goal short of the British league record of goals scored in a season.

The club's success after the first relatively uneventful few seasons in the Scottish Third Division can be explained by the funding of managing director Brooks Mileson, a multi-millionaire. The club has attracted new fans from across the UK and further afield as they continue to win matches. Although some claim that these fans are merely 'fairweather' supporters, shown by the fact that the club only took 500 fans to the title decider against Ross County and had an average attendance of around 1500 (Despite being top of the league for most of the season). The club is committed to several "grass-roots" projects bankrolled by Mileson, such as free tickets for schoolchildren as far afield as Dumfries, and youth coaching. These are indicative of Gretna's desire to become a self-sustaining football club.

Striker Kenny Deuchar has been an important player during Gretna's rise, smashing a number of club and league goalscoring records. Gretna have continue to invest heavily in their playing squad and it is said that they are currently paying the highest salaries outside the SPL and more probably within the top 10 highest salaries in Scotland. Although the population of Gretna is only 2,705 (as of 2001), their current stadium, after the reconstruction holds 6,000 people.

Gretna's first match in Europe was in the UEFA Cup 2nd Qualifying Round against Derry City of League of Ireland. The match ended in disappointment for Gretna however, as the First Division outfit succumbed to a 5-1 defeat; they were then eliminated following a 2-2 draw in the second leg in Northern Ireland.

For much of the 2006-07 season, it looked as if Gretna would again win the division with ease. However, manger Rowan Alexander was forced to step down in March 2007 due to heath problems, and coach Davie Irons stepped up to the manager's position. Gretna's form dipped afterwards and second-placed St. Johnstone went on a good run, leaving the sides only a point apart on the final day of the season. Despite St. Johnstone taking an early lead in their match and looking destined for the Premier League, Gretna managed a goal in the very last minute of the season, giving them a win and ensuring that they will spend season 2007-08 in the Scottish Premier League.

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