Rwanda's Amavubi Stars find themselves drawn with a country that has proved to be a thorn in their flesh once too many times. Uganda has been victorious in three consecutive CECAFA finals against Rwanda - in 2003, 2009 and 2011.
While this is not agonising, more pain comes in the fact that in 2005 and 2007, Rwanda still managed to reach the final, but lost to Ethiopia and Sudan respectively. This means that in recent years, Rwanda holds a record for the 'best losing finalist'.
Uganda Cranes have won Africa's oldest regional football competition a record 13 times, while Rwanda, despite the usual high hopes and expectation from the fans, have won it just once, in 1999 when it was held in Kigali for the first time-It was Rwanda B that triumphed over Kenya.
A fixture between the Amavubi and the Cranes, be it a friendly or a competitive game, is ultimately the most mouthwatering clash in the region, drawing from a historic rivalry that has sometimes gone beyond the pitch.
Yet in this year's CECAFA Cup, both nations find themselves drawn in the same group - Group C, alongside Eritrea and Sudan. A win to whichever side in the cup's first game on Wednesday next week will be a massive boost.
Much as Uganda has mostly emerged on top in these fixtures, last week's friendly in Namboole Stadium shone light on Rwanda's intentions. It's out to prove a point that gone are the days when Uganda simply walked over the fixture.
Rwanda played that game with intent to win. On the other hand, Uganda was mostly on its back foot, mostly, playing with respect. This friendly game gave a glimpse of what we should expect in Wednesday's game.
Yet, the epic may not be about the footballers, but the coaches. Amavubi's Eric Nshimiyimana was appointed the new coach of Amavubi, replacing Milutin Micho Sredojevic, who was fired after a streak of poor results.
Micho was snapped by Uganda as The Cranes head coach, a job he took with both hands, helping Uganda to qualify for African Nations Championship 2014 in South Africa.
Micho told Ugandan press that his motive is "not to revenge" against Rwanda - although I think that is more of talk than reality.
Nshimiyimana on the hand must prove that he deserves the job - so it might not be surprising to see a bit of hot air off the pitch during the competition.
Much as Rwanda and Uganda are the highlights in Group C, a shocker from either Eritrea or Sudan is quite possible.
Eritrea may be the fodder side, but it's hard to tell whether Sudan, a three times champion, will be a walk over.
That said, Rwanda has to kick the monkey off its back and prove that it has what it takes to win this trophy, seeing as it's the biggest chance they have for silverware after failing to qualify for other tournaments.