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2026 WINE.COM

Bracket Challenge

64 brands are selected for a series of matchups that are decided by 3 key factors. Customers who participate are entered into a single sweepstakes drawing for a grand prize

The Challenge Champion!

R4 - Matchup 3 - Brand 2 - Tolani

Tolaini

Pierluigi Tolaini was born in Tuscany, immigrated to Canada in 1956, and spent 45 years building the means to return and make one of Italy's best wines. In 1998 he purchased land in Castelnuovo Berardenga, the southernmost commune of Chianti Classico, brought in famed enologist Michel Rolland, and built a winery from the ground up. With up to 11,500 vines per hectare, the estate's exceptional planting density pushes each vine to produce fewer, perfectly ripe grapes, all of it in service of four red wines with nothing left to chance.

Tuscany, Italy

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How It Works

Vote to Win

Customers who participate are entered into a single sweepstakes drawing for a grand prize

Bracket Winery Sales

Top performing brands by sales will have a leg up on moving to the next round.

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Customer Ratings

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*Limit one vote per customer per matchup

Tournament Sweepstakes

Enter to win One of Four $100 Wine.com Gift Cards

Vote for your favorite wine brands in the Wine.com Bracket Challenge. Every vote is an entry to win one of four $100 gift cards. One champion brand. Let the voting begin. *Limit one vote per customer per matchup.

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Shop The Tournament

Shop your favorite wines from this curated list of partcipating wineries. Shop by price, customer rating, critics' picks, region, and more!

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