The UFC’s 500th event comes from Madison Square Garden this Saturday night and with it comes an absolutely stacked card from top to bottom.

Headlined by the hotly anticipated ‘BMF’ title fight between Jorge Masvidal and Nate Diaz, the rest of the main card features incredibly close to call match-ups between top contenders.

Add in a preliminary card that could see the next light heavyweight contender decided and a host of rising prospects and UFC 244 could well be the best card of the year.

Jorge Masvidal (34-13) vs. Nate Diaz (20-11)

Both Masvidal and Diaz are fairly similar in their approach to fights but I think Jorge Masvidal has more tools to choose from on the feet and that’s where you’d expect this fight to take place.

For all that can be said of Diaz’s cardio and pressure game, Masvidal is sharp on the counter and just as durable as Diaz when on the defensive. Add in ‘Gamebred’s’ power, both in his frame and strikes, and I struggle to see Diaz implementing his suffocating fighting style onto Masvidal successfully or consistently.

Another underrated aspect of this fight is Masvidal’s kicking ability. If Diaz isn’t sharp with his checks when he goes low or blocks sufficiently when he goes to the body, the punishment can easily tally up over a five-round fight.

With all that being said, Diaz is certainly someone who you cannot rule out of a fight. His ground game is exceptional if it hits the mat and his pitter-patter boxing style can drain the will out of the best fighters.

I think that this will be a close fight because both men will want to brawl but Masvidal has proven to be sharper technically with a more diverse arsenal and that should make the difference over 25 minutes.

Pick: Jorge Masvidal

Kelvin Gastelum (16-4, 1 NC) vs. Darren Till (17-2-1)

Darren Till’s decision to move up to middleweight is probably a smart move but Kelvin Gastelum is a really tough stylistic match-up for him to overcome.

Till’s rise to prominence at welterweight was born out of a stinging power behind his strikes and a sharp accuracy with his left hand on the counter.

Against Gastelum, he’ll need to make use of his size advantage and keep Gastelum away but I just can’t see that happening.

Gastelum is durable, a big hitter in his own right and uses combinations and electric hand speed to find his opponents chin often.

Ultimately, the overriding question surrounding this bout is how well either fighter can wear a punch. Will a stop in a draining weight cut allow Till to absorb punches better or has Gastelum’s war against Israel Adesanya taken something from him that he cannot get back?

Unfortunately as a fellow Scouser, I can’t see Till’s distinct lack of head movement not feeding into Gastelum’s strengths in close.

Pick: Kelvin Gastelum

Stephen Thompson (14-4-1) vs. Vicente Luque (17-6-1)

Thompson vs. Luque is seemingly either going to be a range keeping masterclass by the karateka or Luque capitalizing on Thompson’s incresingly-questionable durability.

While Thompson has shown time and time again that his fleet-footed movement and quick kicks can keep him away from danger, he has increasingly been caught with flush strikes in his latest outings.

Tyron Woodley dropped him in each of their bouts, Till dropped him in the final round before Anthony Pettis handed him his first KO loss.

Luque meanwhile is a tough nut to crack as personified in his fight against Bryan Barberena while he’s a thunderous striker with a sneaky submission game to boot.

Again, it could be ‘Wonderboy’ racking up points in the eyes of the judges for three rounds but I doubt Luque goes fifteen minutes without cracking Thompson at some point.

Pick: Vicente Luque

Derrick Lewis (21-7, 1 NC) vs. Blagoy Ivanov (18-2, 1 NC)

While Derrick Lewis is somewhat underrated in his technique, he is perhaps the personification of the heavyweight lottery.

With freakish punching power, he can easily be dominated for all of the fight and land one haymaker that changes the result (see Lewis vs. Volkov).

Against Ivanov, it’s either going to be another one to add to his highlight reel or a gruelling three-round trudge.

Ivanov is a steady fighter that can capitalise on Lewis’ inactivity and he is a tough heavyweight – the man was once stabbed in the heart for goodness sake.

Like all heavyweight bouts, it’s a coin flip thanks to their power but Ivanov has shown to be a decent body puncher and Lewis’ routinely is hurt when hit in the breadbasket. 

Pick: Blagoy Ivanov

Kevin Lee (17-5) vs. Gregor Gillespie (13-0)

Two talented wrestlers meet here and it’s a really tough fight to pick.

Lee has shown himself able to best strong grapplers at lightweight before in the likes of Michael Chiesa but the cut to 155 lbs has proven tough for him and affected his cardio and durability.

Gillespie meanwhile has mauled all of his opponents on the mat albeit at a lower level than Lee while his boxing has looked tight and sharp in the brief flashes we’ve seen.

It’s a big step-up for Gillespie to make but Lee’s questionable cardio combined with what looks like to be another staph infection makes me side with the UFC’s most notorious fisherman. 

Pick: Gregor Gillespie

(Last Predictions: 2/5, Total: 112/189, 59% Success Rate)

(2016: 61%, ’17: 60%, ’18: 58% Success Rate)