Cambridge, MA – One of the most important rap battles of the year — or possibly of the decade if you’re a KOTD fan — is going down at The Middle East in Cambridge, MA (just outside of Boston) on Sunday, May 15.

Hollow Da Don, widely considered to be the best battler of all time, is making his KOTD debut against Pat Stay, the league’s champ from 2013 to 2015, during which he defended the title three times, against Dizaster, Daylyt and Charron. Even before that record-setting run, Pat was considered the best battle MC to ever emerge from Canada.

It’s a battle that KOTD founder Travis “Organik” Fleetwood has been trying to make happen since the earliest days of the league.

“I’ve worked on Pat Stay vs. Hollow for almost 7 years,” he wrote in a recent Facebook post. “ANYTIME I had a budget to work with I was trying to make it happen. It’s literally my 2 personal favourites and a match up that I’ve always said will [be] the best ever stylistically.”

The key word to both Hollow and Pat’s style is versatility. They mix aggression and comedy excellently, and are experts at creatively breaking down the style and personality of their opponents.

Fans got a preview of exactly how good the match-up could be last December when upstart U.K. league Battle Of The Brave popped up out of nowhere and booked the battle. It was a huge first move for the new league, although their inexperience showed when the event was plagued with long delays and last-minute changes. In front of a live pay-per-view audience, the host announced the battle was switching from the scheduled three rounds to one round from each emcee. Later reports revealed that it was payment issues behind-the-scenes that cut the battle short.

Even with all the drama, and in front of a crowd who’d been waiting all day, the two battlers put on one of the best clashes of the year.

Check out the trailer for the main event, and order the live pay-per-view here. The event is scheduled to go live around 2:00 p.m. EST. Check back with DX on Sunday for info on live updates from the event too.

The rest of the card features more big match-ups.

  • Iron Solomon vs. B Magic
  • Head I.C.E vs. Bigg K
  • Math Hoffa vs. The Saurus
  • Pass vs. Money Bagz
  • Gjonaj vs. Danny Myers
  • Bangz vs. DNA
  • Shotti P vs. Xcel

Co-headlining the card is returned legend Iron Solomon against St. Louis punchliner B Magic. For his third battle since his return to the scene, Solomon specifically requested Magic, telling BattleRap.com, “He was one of the people who impressed me when I started watching battle rap again with the idea of getting back in the ring. His style is modern and current, but it has a classic 90s feel to it with the rhythmic delivery and punchlines. I used to be worried about my career arc when it came to picking opponents before, but now I’m more interested in challenging myself creatively and in creating a great moment in hip hop. I think Magic is dope and since he’s thinking about retiring, I want to work with him like that before he does.”

Iron-Solomon-vs-B-Magic-DX

At his best, Magic’s flow and ability to punch in every line are amongst the top in battle rap, though some fans are wondering if he’ll be on his game after a few recent lackluster performances where he didn’t seen motivated. That said, this is one of his bigger match-ups in a while, and he seems confident.

Another highly anticipated match-up is between Norfolk, VA’s Bigg K and Harlem veteran Head I.C.E.

Here’s the trailer for that one:

Math Hoffa and The Saurus will face off in a match-up that was first scheduled for May 2015. Both veteran emcees (from New York and California, respectively) are pioneers of the East and West Coast styles, so there’s a lot riding on a win here in terms of bragging rights.

Another West Coast emcee, Danny Myers, will be facing one of the scene’s most impressive new names, Gjonaj (pronounced “Joe-Nye”), who emerged from Detroit’s Bar Wars league. He caught a huge buzz with his URL Proving Grounds debut, and has since moved over to KOTD, where he’s taken on Dizaster and fellow rising star Psycoses.

Gjonaj at Blackout 6
Gjonaj at “Blackout 6.” KOTD/Banshee.

In their preview of the match-up, BattleRap.com wrote, “No one saw the match-up between Gjonaj and Danny Myers coming, but a look at their recent performances is an indication that it was a good idea and of how high-energy and hotly contested the battle should be.”

Also making his KOTD debut is Queens rapper Money Bagz, against Oakland veteran Pass. Seasoned fans have always considered Money Bagz a threat, but after the collapse of Grindtime NY a few years ago, he was left without a regular platform, and has been quietly killing it with occasional performances in smaller leagues around the East Coast. His opponent Pass is considered one of the frontrunners in the race for the KOTD title, and will need to not only win this battle, but also outdo all of the other contenders vying for a shot if he wants the chain.

DNA is one of the most active battlers in the game right now, making appearances across all of the major platforms as well as many smaller ones, sometimes with multiples battles on the same day. Part of the reason he’s able to be so active is his freestyle ability, which makes him dangerous in any situation. He’s squaring off against Bangz, a newer emcee out of Connecticut whose big personality and unique wordplay have helped him stand out from the ocean of up-and-comers.

Rounding out the card is Shotti P, a new talent from Detroit who impressed in his KOTD mainstage debut in February, against Brockton, MA’s Xcel, who will be looking to put on in his home state.

Dirt vs. Prof-AC has been canceled.

Want more? Check out these 9 battles you should watch before “Massacre 2.”