3 Intriguing NEPSAC Playoff Matchups and Championship Predictions

<!-- wp:paragraph --> <p>The NEPSAC Quarterfinals have concluded, and classes AAA, AA, A, B large, and B small will play their semifinals and final games on Saturday and Sunday of this weekend, respectively.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>I've already done some quarterfinal analysis, which you can read below.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><a href="https://prephoops.com/2026/03/nepsac-quarterfinal-studs/">NEPSAC Quarterfinal Studs</a></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><a href="https://prephoops.com/2026/03/nepsac-quarterfinal-under-the-radar-performers/" id="https://prephoops.com/2026/03/nepsac-quarterfinal-under-the-radar-performers/">NEPSAC Quarterfinal Under-The-Radar Performers</a></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Now, I'll preview three intriguing matchups and will then make predictions for every remaining game in classes AAA, AA, A, B large, and B small.</p> <!-- /wp:paragraph --> <!-- wp:heading --> <h2 class="wp-block-heading"><strong>Three Most Intriguing Matchups</strong></h2> <!-- /wp:heading --> <!-- wp:paragraph --> <p><strong>1. Hoosac School vs. Vermont Academy</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Hoosac upset St. Thomas More in stunning fashion, but they'll have their work cut out for them in a matchup against Vermont Academy on Saturday. Though Hoosac plays a wonderful brand of basketball on the offensive end, they've struggled with quick, shifty, and strong opposing guards, which is exactly how I would describe <strong>[player_tooltip player_id='2568339' first='Kamari' last='Whyte']</strong>. Hoosac will have <strong>Nnadalu Noble</strong> in the paint to clean up some of his drives, but will they have what it takes to limit him on the perimeter? We'll see. Conversely, Hoosac's offensive style involves lots of post ups for both Noble and <strong>Dusan Eric</strong>, who has wonderful footwork and touch in the post. I'm not sure Vermont Academy has what it takes to handle them in the paint, so they'll probably have to bring a double team. This game is a pure contrast of styles and should be an awesome watch.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>2. Cheshire Academy vs. St. George's School</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>St. George's vs. Cheshire will also represent an interesting clash of styles. St. George's plays fast and has all the talent in the world. <strong>[player_tooltip player_id='2611205' first='Kenny' last='Benedict'], [player_tooltip player_id='2341299' first='Dywane' last='Chess']</strong>, and <strong>[player_tooltip player_id='2526248' first='Adriel' last='Cantave']</strong> are all electric in transition and thrive with a head of steam. They certainly move the ball solidly in the half-court, but it's their athleticism and individual talent that really stands out. Cheshire, on the other hand, is greater than the sum of their parts. They don't have the athletes or size that St. George's has, but they play a beautiful brand of basketball consisting of beautiful screening, cutting, and ball movement. <strong>[player_tooltip player_id='2874981' first='John' last='Spinoso']</strong> leads the charge, but <strong>[player_tooltip player_id='3417365' first='Aidan' last='Maguire']</strong>, <strong>[player_tooltip player_id='2546943' first='James' last='Caldarella']</strong> and others also hits shots and runs the show while the system operates. Another clash of styles that should make for a super interesting contest.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>3. King School vs. Holderness School</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>This is an underrated matchup between two teams who are playing excellent basketball as of late. Both have electric offensive systems with tons of shooting, athleticism, and passing ability, and they seem pretty evenly matched in terms of size, skill, and athleticism. King is led by the four-headed monster of <strong>Aj Trimboli </strong>and his brother <strong>[player_tooltip player_id='2571930' first='Ryan' last='Trimboli'], [player_tooltip player_id='1532461' first='Julian' last='Dent Jr.'], and [player_tooltip player_id='2553713' first='Jonovan' last='Bracey'].</strong> They each play a role on the squad, though they don't necessarily have a true big man. Similarly, Holderness is led by a trio of <strong>[player_tooltip player_id='2553725' first='Finn' last='Brennan'], [player_tooltip player_id='2341425' first='Jayvian' last='Cruz']</strong>, and <strong>[player_tooltip player_id='2341360' first='Andre' last='Langley']</strong>, but they also don't play a true big man. Both teams play relatively small and play lots of five-out basketball, so if you like run and gun, high-scoring offensive basketball, this is your game.</p> <!-- /wp:paragraph --> <!-- wp:heading --> <h2 class="wp-block-heading"><strong>Prediction Time</strong></h2> <!-- /wp:heading --> <!-- wp:paragraph --> <p>Now, I'll predict the champions for classes AAA, AA, A, B large, and B small.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>Class AAA: Newman School</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>I didn't have to think too hard about this one—Newman is a complete wagon. There's no weakness on either side of the basketball and they have both the talent and poise to win when it matters most, even if open shots aren't falling or the whistle isn't going their way. They have 5+ guys who can be their leading scorer any night, and it's because they play an egalitarian offensive system centered around passing, cutting, and perimeter shooting. They have [player_tooltip player_id='2341371' first='Chase' last='Geremia'] coming off the bench—what more do I need to say? Defensively, they play their behinds off and have the depth to overcome foul trouble or injury. Anything can happen in one game, but they're the clear favorite.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>Class AA: Cushing Academy</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>I really want to give another team a shot at taking out Cushing, but I just can't bring myself to do it. Kimball Union is feeling great after a really nice win over Winchendon, and they have guys like <strong>[player_tooltip player_id='2546965' first='Zach' last='Romich']</strong> and <strong>[player_tooltip player_id='2452977' first='Brandon' last='Arnold']</strong> who can get hot at any point from three. Cheshire plays very aesthetically pleasing basketball, but they probably don't have the size to compete with <strong>[player_tooltip player_id='2470882' first='Theo' last='Edema']</strong> or the point-of-attack defense to stop <strong>[player_tooltip player_id='2465117' first='Ryan' last='Moesch']</strong>. And St. George might be able to match Cushing's talent, but I don't have as much confidence in them to execute down the stretch of a game and make plays when they matter most, especially with some of the inexperience they have. Most importantly, none of those teams have [player_tooltip player_id='2465117' first='Ryan' last='Moesch']—need I say more?</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>Class A: Phillips Exeter Academy</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Exeter is obviously not your typical 8-seed. They're playing their best basketball of the season right now, and I just think they've struck something special with what they have going on. They've employed the "wheel" concept, commonly seen with the Memphis Grizzlies, Miami Heat, Cleveland Cavs, and other NBA teams. Essentially, whenever a drive occurs, everybody moves in the direction of the ball, which is incredibly difficult to guard. As a result, they score on tons of corner and 45 cuts and are almost never playing against a set defense. <strong>[player_tooltip player_id='2829417' first='Cole' last='McClure']</strong> leads the charge on the offensive end with his ability to score in isolation, but <strong>Shawn O'Neill</strong> runs the show like a true point guard and <strong>[player_tooltip player_id='2696663' first='Christian' last='Chartier']</strong> can also hit shots from all over the floor. They're all bought in, and they're HOOPING right now. A rematch with Phillips Andover in the championship would just be wonderful.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>Class B Large: St. Mark's School</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>St. Mark's will have their work cut out for them with a big and tough Master's squad. But <strong>[player_tooltip player_id='2341443' first='Luca' last='Palermo']</strong> and <strong>[player_tooltip player_id='2553759' first='Donovan' last='Clement']</strong>, St. Mark's front line, are a great duo to handle it, and they have the size and strength to limit Master's in the paint. And with <strong>[player_tooltip player_id='2878625' first='CJ' last='Farrell']</strong> and <strong>Alex Echevarria</strong> running the show, I trust their ability to get good shots and execute down the stretch of basketball games. They have a well-rounded squad and can beat you from all three levels. Rivers and Canterbury are both talented teams as well, but I don't see them having what it takes to overcome St. Mark's talent and size. I probably feel more confident about this pick than any other.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong>Class B Small: Holderness School</strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p>Holderness has a really fun matchup with King School before a potential face-off with Kingswood-Oxford in the finals, and I think they have the talent and coaching necessary to take it home. I already mentioned <strong>[player_tooltip player_id='2341425' first='Jayvian' last='Cruz'], [player_tooltip player_id='2553725' first='Finn' last='Brennan']</strong>, and <strong>[player_tooltip player_id='2341360' first='Andre' last='Langley']</strong>, but Holderness even has some depth with <strong>Micke-Andy Mera</strong> and <strong>[player_tooltip player_id='2547044' first='Mason' last='Paquette']</strong>, two guys who can erupt offensively on any given night.</p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p> <br></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><strong><br></strong></p> <!-- /wp:paragraph --> <!-- wp:paragraph --> <p><a href="https://prephoops.com/2026/03/nepsac-quarterfinal-under-the-radar-performers/" id="https://prephoops.com/2026/03/nepsac-quarterfinal-under-the-radar-performers/"><br></a><br></p> <!-- /wp:paragraph -->