Like all journeys, you have to start at the beginning, and the beginning of the rivalry between The Dudley Boyz and The Hardy Boyz technically starts in September 1999. 

Fresh off of their legendary run in ECW, Buh Buh Ray (yes, that is what his name was because of his stutter) and D-Von were ready to take over the World Wrestling Federation, and if they needed to put a few people through tables, that wouldn’t have been a problem. Their first actual feud that they were involved in was with The Acolytes, Bradshaw and Faarooq, who were already known for being able to beat the color out of teams that came from other promotions, just look at what they did to The Public Enemy, and to give themselves a bit of momentum heading into the 1999 Unforgiven pay-per-view, The Dudley Boyz needed a win, and that win came over a young Matt and Jeff Hardy.

At this point in time, Matt and Jeff had already had a brief run with the WWE Tag Team Championships, but they weren’t the world beaters that they would go on to be, and they hadn’t even showcased how well they could use ladders as their tag team ladder match with Edge and Christian was still a few weeks away. They were a team that could easily make the former ECW guys look good, while also being trusted enough in the ring, even at a young age, to get themselves over as well.

The first official match between The Dudley Boyz and The Hardy Boyz, who were then known as The New Brood and had Gangrel as their manager, took place on the September 20, 1999 edition of “WWE Raw,” with Bradshaw and Faarooq scouting their opponents for the pay-per-view on commentary. It’s a match that really is a time capsule and a look into a different era. The Dudleys are still wearing their tie dye gear, something that would be changed by the turn of the millennium. Stevie Richards was even at ringside dressed as a member of the Dudley clan, and the match ends after two-and-a-half minutes with Matt eating a 3D to absolutely no response from the crowd.

It’s not a five-star classic, it’s not even a classic if we’re being perfectly honest, but it is historic for the fact that it was the first meeting between two teams who go on to have Hall of Fame careers, and was also first match that The Dudley Boyz had ever wrestled on “Raw.” By the start of 2000, The Dudleys had earned the respect of the WWE locker room after withstanding The Acolytes, The Hardys had catapulted themselves into the spotlight as one of the most exciting tag teams on the planet, and a collision course on one of the biggest stages that WWE could offer was on the horizon. All Buh Buh Ray and D-Von had to do was bring the wood.