UFC Fight Night: Grasso vs. Shevchenko 2 Preview and Predictions

After a three-event tour spanning three different continents, the UFC lands back at its home base at the T-Mobile Arena in Las Vegas on Saturday, Sep. 16 to host UFC Fight Night: Grasso vs. Shevchenko 2. The event has also been dubbed Noche UFC, as the event takes place on Mexican Independence Day. The headlining affair will be the women’s flyweight title rematch between Mexican champion Alexa Grasso and the Kyrgyzstani former champ Valentina Shevchenko.

The two women last met at UFC 285 six months ago, and Graso upset the long-reigning champ when she submitted Shevchenko in the fourth round. The UFC set up an immediate rematch, and the proud Mexican champ will be looking to keep the belt in her native country on this special day. Shevchenko, who hadn’t lost in nearly six years, is determined to get back the belt she had held since Dec. 2018.

The co-main event features 13-fight UFC veteran Kevin Holland, as he takes on surging Australian prospect Jack Della Maddalena in a welterweight battle. Holland just fought seven weeks ago, when he scored a first-round submission of Michael Chiesa. Della Maddalena, on the other hand, is on a 15-fight winning streak, having not lost since he dropped his first two MMA bouts. He last fought Bassil Hafez on short notice just nine weeks ago, when he scored a split decision. Both men are looking to climb the UFC welterweight rankings.

UFC Fight Night: Grasso vs. Shevchenko 2 airs live in its entirety on ESPN+ starting at 7 p.m. ET.. Combat Press writers Dan Kuhl and Matt Petela preview the action in this week’s edition of Toe-to-Toe.

Alexa Grasso pulled off one of the sport’s biggest upsets when she claimed the title from Valentina Shevchenko in the pair’s first meeting; can she beat the future Hall of Famer again to make it 2-0?

Kuhl: Alex Grasso pulled off one of the biggest upsets in recent history, when she entered the Octagon at UFC 285 to face Valentina Shevchenko as the +575 underdog, only to walk out the newly minted flyweight champion. Shevchenko had not lost in five-and-a-half years and was up 29-28 on all three scorecards going into Round 4. Then, in the final minute of the round, Shevchenko threw a sloppy spinning back kick as Grasso was coming in, missed, and got her back taken immediately. Within about 30 seconds, Grasso locked in the rear-naked choke – technically a face crank – and, eventually, forced Shevchenkon to tap. It was a thing of beauty.

The way that fight went was a lot of forward pressure and standing wrestling by Grasso. She brought Shevchenko into her world, and, when it counted, started to dictate the pace. Will this happen again? Likely not, but it’s not quite that simple.

Shevchenko is a lifelong combat sports athlete, she has made a lot of money, and she could retire comfortably at any time. She is also 35 years old and has a whopping 88 professional combat battles under her belt. Needless to say, she has a lot of miles on the chassis, and, in the last fight with Grasso, she seemed uncharacteristically flat as the fight entered the championship rounds. Entering this rematch, she is still the favorite, but she is only the -160 betting favorite, which is a significant difference from the last meeting.

Grasso, on the other hand, is only 30 years old, has a deep gas tank, has only 19 pro fights under her belt, and has a lot of runway ahead in her career. She may have been down two rounds to one, but she came into that fourth round as confident as ever. I have a feeling we may see much of the same in the rematch.

There is a psychological factor to losing, especially as a longtime champ who is approaching the latter years of a long and storied career. There isn’t really anything left for Shevchenko to prove, and, while I will never question where a champ of her caliber’s heart is, heavy is the head that wears the crown. Is she really ready to start a second run as the queen, or is she ready to start her retirement tour?

I’m going with the latter. Shevchenko is one of the greatest mixed martial artists in history, but I feel we are seeing a changing of the guard. Grasso is carrying the entire country of Mexico on her back, and, after her fellow countrymen Brandon Moreno and Yair Ridriguez lost their titles a couple months ago, there is an X-factor that she has to add to her championship momentum. I have Grasso dragging this one deep, before eventually scoring another submission win in the championship rounds.

Petela: I agree with Dan on this one, Alexa Grasso will retain her title and move to 2-0 against Valentina Shevchenko. I fully admit that I was more than a little skeptical of Grasso’s chances in the first matchup, I didn’t see a path to victory for the Mexican star and thought it would be either Manon Fiorot or Erin Blanchfield that eventually dethroned the long reigning Shevchenko. I severely underestimated the striking advantage that Grasso had and thought that, if she did start to do damage on the feet, Shevchenko would turn it into a submission grappling contest where she would be head-and-shoulders above her opponent. I sure was wrong about that. Not to toot my own horn too much, but I successfully predicted that Grasso would get her first career submission win over Joanne Wood, but, still, I thought that she was several notches below Shevchenko.

I am not going to make the same mistake twice. I still think a prime Valentina Shevchenko is far and away the best women’s flyweight of all-time, but she is a shade past her prime, and Alexa Grasso is entering her prime now. An improved Grasso will be a clear step ahead on the feet of an aging Shevchenko, and she will be able to fend off takedown attempts much easier this time around. This one ends in a lopsided decision win for the incumbent champion and begins the next era of the flyweight division.

Jack Della Maddalena squeaked by short notice replacement Bassil Hafez in his last fight; can the highly touted prospect score the biggest win of his career against Kevin Holland?

Petela: Before his last fight, I thought Jack Della Maddalena was headed straight to the top of the welterweight division. However, that last outing against Bassil Hafez was not his finest performance. This is definitely a major step-up, and I totally understand why people are hesitant to think that he is ready for an opponent of this caliber.

I think Della Maddalena rises to the occasion here in a big way. Kevin Holland is very good, and I think that will actually bring out the best in JDM. Wherever the fight goes, I think Della Maddalena will have the advantage. He’s a well-rounded prospect, and I am confident that the Hafez fight was a fluke. The short-notice replacement overachieved while Della Maddalena underperformed. This one probably goes all 15 minutes with a wide unanimous decision victory for the Aussie.

Kuhl: I really don’t believe Jack Della Maddalena’s split decision win over Bassil Hafez showed any holes in his game. Rather, it showed the ability for him to take on a super-short-notice bout against a guy who is hungry to stake a claim in the UFC. Hafez entered the cage five months after winning the Fury FC welterweight title, and, traditionally, this leads to a full head of steam. He had nothing to lose, and fought as such, but JDM still had the ability to keep his five-and-a-half-year winning streak alive.

Kevin Holland, on the other hand, is a UFC veteran with black belts in Kung Fu and Brazilian jiu-jitsu. Since dropping down from middleweight to welterweight, he has gone 4-2 with no decisions, and, most recently, scored back-to-back stoppage wins over fellow veterans Santiago Ponzinibbio and Michael Chiesa. His last two losses were to Khamzat Chimaev and Stephen Thompson, who are both currently ranked in the top seven. By all accounts, on paper, Kevin Holland should win this fight. So, why do the sportsbooks have this one almost even?

Styles make fights, and Holland has a style that is, for lack of a better word, stylish. He is flashy, dynamic, and fun to watch. Della Maddalena, however, is more of a gritty, utilitarian type of fighter. He is a forward-pressing boxer who is tough as nails with hands of steel and powerful wrestling.

It’s time for Della Maddalena to break through with a big win over a big win, and, after 15 minutes, I, too, think he picks up the decision win over Holland.

What one fighter’s UFC career is on the ropes at this event?

Kuhl: I never thought I would say this, but Valentina Shevchenko may see her final walk to the Octagon on Saturday. Not that she would be cut or anything after two losses in six years, but she has nothing left to prove, and, if she loses again to Grasso, she will likely not get an immediate third shot at the Mexican champ, and getting back in line, is not a very favorable position for the long-reigning champ. She could easily retire as one of the greatest fighters ever.

Petela: Raul Rosas Jr. could be on the chopping block if he doesn’t get a win this weekend. The young prospect fell in his last outing and gassed out badly in the second round. If he doesn’t beat an opponent who is tailor made for him this weekend the experiment might be over for the time being with the teenager and he will find himself back on the regional scene trying to fix the holes in his game, most notably his cardio and energy management.

Which fight is the sleeper match-up on this card?

Petela: Roman Kopylov vs. Josh Fremd. Kopylov is on a three-fight winning streak and he has scored knockouts in all of those victories. Meanwhile, Josh Fremd has won two in a row and looks to be turning the corner in his career at age 29 as he really enters his physical prime. These two middleweights are both in position to start opening fans’ eyes to their upper bound limits with a win. Not only will this fight build a good bit of momentum for the victor but it will also be a fun fight as these two spend several minutes standing and trading in a highly technical brawl.

Kuhl: The return of Tracy Cortez, as she faces Jasmine Jasudavicius, should be a great fight. Cortez has been on the bench for 16 months, but is still riding a 10-fight winning streak after her only career loss in her pro debut. Jasudavicius has won back-to-back battles in 2023, and these ladies are in a prime position to put on a fun fight

Who takes home the “Performance of the Night” honors?

Kuhl: Jack Della Maddalena. He may have barely won his last fight, but it’s always a crapshoot taking on a short-notice replacement. JDM is a wrecking machine, and, when he stops Kevin Holland, he’s going home with some extra dough.

Petela: Jasmine Jasudavicius. She is going to spoil the return of Tracy Cortez and she’s going to do it in style. She’s not known as a finisher, per se, but I expect big things from Jasudavicius this weekend. Cortez is a mid-level fighter, at best, and she will be rusty early because of the extended time away from the cage. Jasudavicius will clip her early in the first round, at which point she will take down a wobbly Cortez and submit her with a rear-naked choke. The old club-and-sub will be just what the Canadian needs to earn herself a post-fight bonus.

Pair this card with…

Petela: I mean, the reason behind this fight card is Mexican Independence Day so celebrate appropriately with your favorite Mexican food dish. I’ll be going soft tacos with ground beef and of course pile on the sour cream. Add a few Modelos and you’re in great shape to kick back and enjoy the event.

Kuhl: I am 100-percent on board with the Mexican food theme, but I’m going more authentic Mexican. A combination of lengua and cabeza tacos with onions and cilantro, a squeeze of lime and some salt will be the perfect pairing for some cans of Tecate. I would also suggest some crispy chile rellenos smothered in green chile and, of course, some chicharrones.