They have not and I doubt they will see each other this year. The Father Ryan tournament might be the only chance but I am not sure either will be in attendance.
They have never wrestled, or if they did then Howard was too young for it to have been a real gauge. Skylar will be at F.R. Tourney again. McCallie hasn't come last couple years though. I know it's a message board and it's fun to talk about "what-ifs," but it's not slated to happen and Skylar will graduate this year. My opinion would be Skylar controlling everything, and I attribute it mostly to age/physical maturity. I wish Skylar from this season and Kramer from last season could have battled. Skylar was lighter this spring though, so they each got their easy paths to the state titles @ 220 and 285.. Maybe it would be tight in Skylar from this season and Howard when he's a Jr or Senior.... it's not even really a debate though because they won't see each other unless McCallie makes a drive to GP West tourney in January like Baylor did last year.
Howard looks good and has creds with NHSCA... against other freshmen. He's elite for his age and for the overwhelming majority of the country. He's still two years younger and frankly outmatched when it comes to physicality and pure athletic ability. You could have seen a comparison if Howard had gone to Super32, but he didn't. Skylar did and in only his second national tourney he placed 4th (his previous was 5th earlier in the year at NHSCA). His losses at Super32... to #1 nationally ranked HWT (Catka who's also a Sr) in a 0-8 MD. The was the closest anyone came to Catka, except when he beat the #2 nationally ranked kid 8-2 in the finals. Skylar's other loss was in 3rd place match when he got caught by a big boy from PA. His wins though were crazy impressive against a slew of state champs including a pin vs. Ohio state champ and then beating PA state champ, prior year Super32 finalist and #5 nationally ranked kid from PA. These are the best kids in ALL grades across the entire country.... Skylar is one of those elite wrestlers. Based upon what I've seen of Howard, he is one as well that is still maturing. I'd take Skylar 99 out of 100 times at this specific point in time though (with the one loss being a DQ because Refs tend to overreact to 250lbs+ flying through the air :) All kidding aside, I love that we have two kids this talented in the state of TN. I hope the talent levels continue to rise and it raises the profile of our collective wrestling and encourages other younger kids to be the next "Coffey" and next "Howard!"