1998-99 was the first season of the new Scottish Premier League and Dundee proudly took their place thanks to a promotion gained by a brilliant title win in May, which saw them lose just six games to top the First Division by five points.
Manager Jocky Scott had taken over from John McCormack halfway through the title-winning campaign and, as he geared his side up for a crack at the SPL, he managed to retain the services of deadly strike duo James Grady and Eddie Annand, who had formed a formidable partnership that saw them hit 31 goals between them on the way to the championship.
Goalkeeper Robert Douglas was being tipped for big things after a number of fine performances, while former Aberdeen defender Brian Irvine and former Hibernian star Willie Miller made up an experienced backline. Future club legends Gavin Rae and Barry Smith were well on the way to making names for themselves, while less familiar names like Stephane Pounewatchy and Darren Magee gave pub quiz writers of the future some ammunition with fleeting appearances.
Dundee’s kit for the season was an all-blue top with red and white trim, white shorts with red trim, and blue socks with red hems. It was sponsored by Scottish Hydro Electric, which later became SSE Hydro (known for sponsoring Glasgow’s large music arena) and was manufactured by Durham-based sportswear company Avec.
The season started poorly for the Dee, losing their first four matches, including a League Cup defeat at home to Second Division Alloa. However, a 1-1 draw at home to Celtic, courtesy of a 90th-minute penalty from Eddie Annand, sparked them into action and they went unbeaten in six of their next eight games.
On 22nd of November they faced local rivals Dundee United at Tannadice. Dundee were in seventh place but just two points separated them from United, who sat in eighth, level on points with bottom-of-the-table Dunfermline. With the match seemingly heading for a 0-0 draw, James Grady scored a stunning volley from 20 yards in the 82nd minute to give them a crucial victory and send the away fans wild.
By March, Dundee were right in the thick of a relegation dogfight, exacerbated by a 2-0 defeat to bottom club Dunfermline. However, that result seemed to give them a kick where it was needed, and they embarked on a run that saw them lose just twice in their last nine games, winning six. The highlight was another stunning victory at Tannadice as Brian Irvine and James Grady gave them a famous 2-0 win.
Having looked in danger of relegation in March, the Dark Blues finished the season in fifth place, just one spot off European qualification. They towered 12 points and four league positions above Dundee United, and claimed the city’s bragging rights for at least the next few months.
Most incredibly of all, though, it turned out to be their highest league finish since 1974, and one that still hasn’t been bettered nearly 20 years later.