The 2026 New England boys prep Small School tournament is the most top-heavy of the three brackets.
That doesn't mean there won't be upsets.
Come Wednesday, the quarterfinals will get underway. No. 1 Holderness will take on No. 8 Pomfret, No. 2 Winchendon will host No. 7 New Hampton, No. 3 Canterbury will face No. 6 St. George's and No. 4 Rivers will clash with No. 5 Berkshire.
I love doing predictions. I went 13-8 throughout the three rounds and three tournaments last season, redeeming myself with a 2-1 record on championship day. I've gone 13-8 the last two seasons.
Here's to hoping I can get to 14 or 15 correct selections this season.
Let's dive in.

No. 1 Holderness vs. No. 8 Pomfret
I've been fortunate to see former Milton Academy coach Paul Cannata at a few rinks over the last month. He always brings up how good Pomfret was against Dexter when the two met on Feb. 4, with the Shields winning, 4-2. There's no doubt Pomfret has the talent to compete with Holderness. Postgrads Giacomo Caliri (Cranston, R.I.) and Cam Peltz (Simsbury, Conn.), seniors Rich Cavanagh (Warwick, R.I.), TJ Swinson and Will Norton (Lynnfield, Mass.), and junior Nathan Dono (Sturbridge, Mass.) are a deep offense. Senior Ian Sherman (Brooklyn, Conn.) is a stout, No. 1 defenseman. And senior Joey Mitchell is a strong goalie with a 2.89 goals-against average and a .915 save percentage. Pomfret is better than a No. 8 seed.
But there's a reason the Griffins are a No. 8 seed. They've gone 3-6-1 over their last 10.
Holderness is deeper up front and on defense, and is fresh off taking down Kimball Union to win the Lakes Region championship.
Holderness won the first matchup, 2-1, on Dec. 18. The Bulls should take the second, too.
Prediction:Â Holderness wins, 4-2.
BOYS BRACKETS: Elite 8 field | Large School field | Small School field

No. 2 Winchendon vs. No. 7 New Hampton
I talked about this in our bracket reaction, but New Hampton is amazing at playing up to the competition. The Huskies make a lot of sense as an upset pick. Senior forwards Johnny Niemela, Dylan Podergois and Matthew Homer can match up with anyone.
But can New Hampton match Winchendon's depth? And can it keep the No. 2 offense in prep at bay?
Ironically, New Hampton did in its first game of the season, shutting out Winchendon, 1-0. But that was on Dec. 3. I lean no on both on March 4.
The Wapitis boast three players above 50 points and six who are averaging over a point per game. And those six don't even include seniors Edouard Cantin, Kaden Kern (Lincoln, R.I.), Steven Khonroo and sophomore Drew Short (Lunenberg, Mass.), as all four players are on the verge of being a point per game.
New Hampton will be competitive. But Winchendon's offense will be too much to handle.
Prediction: Winchendon wins, 6-3.

No. 3 Canterbury vs. No. 6 St. George's
St. George's was an up-and-down team throughout the season, but actually ended well, going 6-1-2 in its final nine games. The Dragons boast senior Max Donatelli (Barrington, R.I.), who notched 50 points this season and who will be the best player in the game.
I just don't see St. George's being able to compete with Canterbury's depth and age. Postgrads Jack Mceleney (Woburn, Mass.) and Jack Lee (Woburn, Mass.), and seniors Seamus McMakin (Burlington, Mass.), Gaines Clonts and Britton Bethard have been effective scorers. On defense, senior Tommy Browne has been one of the top defenders in the region and senior Logan Martel has generated offense.
Canterbury is also better defensively. Senior Cody Hew, with a 2.42 GAA and a .932 save percentage, isn't to be picked against in the first round.
Prediction:Â Canterbury wins, 3-1
PREVIEWS: Elite 8 |Â Large School | Small School

No. 4 Rivers vs. No. 5 Berkshire
Both of these teams have fantastic goaltending. Berkshire's Alex Kim (Leonia, Mass.) has a 1.70 GAA and a .926 save percentage. Rivers' Derrick Huang (Carlisle, Mass.) has a 1.80 GAA and a .947 save percentage, while Will Torres (Framingham, Mass.) has a 2.39 GAA and a .920 save percentage. I have those goalies canceling themselves out and having outstanding games.
This game will come down to whether or not Rivers, a stingy, physical team, can shut down Berkshire's big guns in seniors James McMurray, Jonah Rainisch and Matt Lacombe (Marlboro, Mass.).
This one is a coin flip. I say Rivers does.
Prediction:Â Rivers wins, 2-1, in overtime.


