Can Dundee ever again become the city’s top club or have United so cemented their position as top dogs that the Dark Blues’ bark will remain worse than their bite?
Only brave souls would suggest that the Dee, after a period of United dominance stretching around fifty years, could soon regain their former status.
On Sunday though they have an opportunity to begin the long haul back towards evening the score in competitive matches, where the Tangerines have 83 wins to Dundee’s 55 in their 183 meetings.
The first Premiership battle in over five years could dramatically shape the season for both sides’ managers.
The clubs last did battle in the Championship in 2019, but meeting in the top flight is of a far more intense magnitude, with frailties and weaknesses mercilessly exposed.
United boss Tam Courts, picking his derby team for the first time, must find someone capable of hitting the net.
Dundee manager James McPake also must ensure that among the plethora of strikers available to him, one of them can locate his shooting boots.
Tannadice, with a baying crowd right on top of the players, can test the mettle of the most experienced competitor, so calm heads are needed; no easy task amid the frenzied atmosphere in what will be a cauldron of passionate intensity.
The first wild tackle putting an opponent up in the air can set the tone for subsequent mayhem and madness and result in the loss of composure.
The key men for me in what should be a pulsating 90 minutes are Charlie Mulgrew and Mark McNulty for United
And if he can make a rapid recovery from his injury, Charlie Adam – and Leigh Griffiths – for Dundee.
Dundee have their strongest squad in years for this game and a fit Adam, with his quick brain and range of passing, could exploit any defensive laxity from United.
Griffiths may not be as sharp as he was due to lack of competitive football, but he strikes the ball fiercely and accurately and has the football nous to find the crucial half yard of space which can provide goals.
Both men also deliver deadly danger from free kicks.
For United, Mulgrew’s cool head under pressure could be crucial.
He has strong leadership qualities and the ability to find passes out of defence to relieve pressure on his back line and open up attacking possibilities.
McNulty missed a sitter at St Mirren last week, but his speed off the mark as he bore down on goal showed that he has the pace and mobility to evade defenders.
If he can find the lethal touch to match his football intelligence and movement then United could prosper.
The unveiling of Jim McLean’s statue on Saturday night will add to the rich tapestry of this city derby and the intense rivalry between the clubs.
Had Jim been appointed as manager at Dens instead of being allowed to cross the road to Tannadice, United may never have reached the prominence that they have and Dundee might have remained the number one club in the city.
On such decisions is football history made.
Who makes our Dundee United and Dundee combined XI ahead of derby day at Tannadice?