Both men were victorious in their final Strikeforce fights but they still have plenty left to prove if they want to truly make their make in the middleweight division. How can either man pull it off?
Record: 14-4 overall, 0-0 in the UFC
How he got here: Tim Kennedy actually began training in MMA at a very young age alongside Chuck Liddell and John Hackleman at The Pit. After lengthy amateur career, he would lose his professional debut to Scott Smith via cut.
Kennedy would make his big splash at Extreme Challenge 50, winning three fights in one night to capture the tournament title and defeating Jason "Mayhem" Miller in the process.
The native Texan proceeded to enlist in the military where he became an Army Green Beret, deploying overseas and not fighting for three years.
Upon his return to MMA, Kennedy would win three straight bouts before losing a rematch to a much improved Miller. After not fighting in 2008 due to overseas commitments, he would make his Strikeforce debut in 2009, easily handling UFC veteran Nick Thompson.
After scoring two more impressive victories, he would be given an opportunity to win Jake Shields' vacated middleweight title against Ronaldo Souza. The fight would take place primarily in the stand-up and Souza surprised many with his aggression, winning a unanimous decision.
Kennedy bounced back by dominating Melvin Manhoef and he proceeded to ask for a fight with Robbie Lawler to get him back in the title picture. He got his wish and made the most of it, outgrappling the veteran to earn another crack at the belt. This time, he would once again lose a decision, but it would be to new champion Luke Rockhold and it was much more one-sided.
He destroyed Trevor Smith in his fight Strikeforce fight to prepare himself for his UFC debut this weekend.
How he gets it done: Kennedy will want to avoid going to the canvas against Gracie, but that's not a shocker. Gracie is a world champion submission specialist. He'll also be at a reach disadvantage so he'll have to be conscious of his location, not staying too far to land anything and not getting too close where he could be kneed or potentially get stuck in a defensive situation in the clinch or defending trip takedowns.
Expect Kennedy to push forward and try to find the sweet spot in the striking department where he can work some short kicks and particularly land his punches. He's not the most powerful middleweight out there, but he's got enough talent standing up to do some damage if Gracie can't take the fight to the ground.
As long as he doesn't give Gracie easy takedowns, he definitely has a good chance of pulling this one off.
Record: 6-1 overall, 0-0 in the UFC
Key Losses: Muhammed Lawal (Strikeforce: Barnett vs. Kharitonov)
How he got here: The grandson of the great Carlos Gracie, Roger Gracie got his start like any Gracie, in Brazilian jiu-jitsu. He was awarded his black belt in 2003 by Renzo Gracie and after a third place finish in the 2003 Abu Dhabi Combat Club, he began his devastation of the BJJ ranks. Gracie returned with a vengeance in 2005, winning both the 88-98 kilogram division as well as the Absolute division gold medals and submitting every opponent in his path including highly decorated BJJ practitioners like Shinya Aoki, Fabricio Werdum and Ronaldo Souza.
Gracie began his mixed martial arts career a year later, submitting Ron Waterman in Vancouver as well as Yuki Kondo two years later in Japan.
He would make one last terrific run in jiu-jitsu, winning the world championship multiple times at the Mundials in Brazil in both 2009 and 2010 at the Super Heavyweight division as well as the Absolute division before announcing that he was going to focus on MMA.
The world-renowned BJJ champ made his Strikeforce debut in 2010, surprising former UFC champion Kevin Randleman with his improvements in striking before taking the fight to the ground and ending it via rear naked choke. He would follow up that victory with an absolute destruction of South African Trevor Prangley in the first round this past January.
He battled "King Mo" Lawal in his final light heavyweight bout and was caught with a big right hand en route to receiving his first career loss. After winning a superfight at the ADCCs, Gracie returned to MMA, this time at 185 pounds where he dismantled both Keith Jardine and Anthony Smith in consecutive Strikeforce fights.
Now, he's getting another step up in competition and is hoping to make the most of it.
How he gets it done: There's absolutely no doubt that Roger Gracie wants this fight to go to the ground where he can work his magic on the canvas. What's going to make this difficult is that Kennedy has a competent ground game and could use his wrestling in reverse to keep Gracie standing, where he's still a bit of a fish out of the water..
Gracie has a long, lanky frame. If he were a decorated striker, this would be a huge strength for him but he's still got a long ways to go before he's knocking opponents out standing. That being said, his head kicks and knees are still dangerous and he could always catch Kennedy napping if he doesn't throw them too often.
They key for Gracie will be to avoid standing in the pocket. From a distance he can work some of his kicks and stay outside of Kennedy's range. If the former sniper gets too close, Gracie will have to be clinching and either looking to utilize a trip takedown or instead work knees and elbows from up close.
Pulling guard would not be a horrible option either as Gracie has suffocating hip pressure and he can force Kennedy to stay on the ground with him just like he did against Keith Jardine. If he can put Kennedy on the ground, he can't be too methodical as his opponent will be working like his life depends on it to get back to his feet.
Who will come out on top at UFC 162? Tell us your predictions in the comments below!