March Bourbon Madness: Best-of-the-Shelf Challenge—First Round Matchups 29-32

Opening Pour

The Final Four of Round One

The last pours of the first round are in the books.

By this point, fatigue is real. Subtle differences matter more. Texture separates contenders. And a couple of heavy hitters had to survive gritty matchups to advance.

Here’s how the final four blinds of Round 1 played out.


🥃 Matchup 29 — Blind

CC vs. B

Blind Tasting Notes

CC

Color: Light mahogany
Nose: Lighter than expected — caramel, vanilla, oak
Palate: Warm caramel and oak lead; baking spice and tart cherries follow
Mouthfeel: Decent
Finish: Tart cherry, oak and caramel

Score: 83.65


B

Color: Deep copper
Nose: Rich creamy caramel, chocolate and nutmeg
Palate: Milk chocolate leads caramel and baking spice
Mouthfeel: Creamy and substantial
Finish: Solid, with spice and caramel rounding it out

Score: 84.20


Reveal & Result

CC: Old Forester 1910 (#6)
B: High West Chardonnay Cask (#59)

Winner: High West Chardonnay Cask
➡️ Advances to Round 2

Post-Matchup Thoughts

This one surprised me. 1910 is usually reliable, but it showed up a little restrained here. The High West brought richness and texture that carried the edge.

What decided it:
Mouthfeel and chocolate-driven depth.


🥃 Matchup 30 — Blind

EEE vs. I

Blind Tasting Notes

EEE

Color: Deepest copper
Nose: Butterscotch, caramel, nutmeg, light oak
Palate: A butterscotch bomb — caramel and nutmeg in reserve
Mouthfeel: Mildly creamy
Finish: Toffee and nutmeg linger

Score: 87.34


I

Color: Light copper
Nose: Buttery toffee, nutmeg, vanilla, mild oak
Palate: Caramel and baking spice with a touch of peanut
Mouthfeel: Mid-level
Finish: Spice and caramel dominate

Score: 79.96


Reveal & Result

EEE: Jack Daniel’s Distillery Series Oloroso Cask (#27)
I: Cooper’s Craft 100-Proof (#38)

Winner: Jack Daniel’s Oloroso Cask
➡️ Advances to Round 2

Post-Matchup Thoughts

This wasn’t particularly close. The Oloroso finish delivered concentrated dessert richness and control. It felt composed and confident.

What decided it:
Layered sweetness and balance.


🥃 Matchup 31 — Blind

BBB vs. F

Blind Tasting Notes

BBB

Color: Mid-copper
Nose: Proof and oak lead; brown sugar trails
Palate: Sweet brown sugar with strong cinnamon and light caramel
Mouthfeel: Silky
Finish: Shorter than hoped; brown sugar and cherry

Score: 83.44


F

Color: Solid mahogany
Nose: Brown sugar, nutmeg, crème brûlée
Palate: Rich buttery layers of caramel, chocolate and nutmeg
Mouthfeel: Full and rich
Finish: Long, layered, and persistent

Score: 85.50


Reveal & Result

BBB: Four Roses OESO Barrel Strength (#11)
F: Woodford Reserve Double Oaked (#54)

Winner: Woodford Reserve Double Oaked
➡️ Advances to Round 2

Post-Matchup Thoughts

OESO came in strong, but Double Oaked did what it does — richness, texture, dessert weight. It simply lingered longer and felt more complete.

What decided it:
Depth and finish length.


🥃 Matchup 32 — Blind

L vs. FF

Blind Tasting Notes

L

Color: Light copper
Nose: Ethanol and dustiness, but brown sugar and caramel hiding
Palate: Heavy spice with brown sugar and toffee
Mouthfeel: Solid and rich
Finish: Caramel and baking spice

Score: 80.62


FF

Color: Mid-copper
Nose: Mixed berries, light oak, vanilla
Palate: Cinnamon up front, berries, caramel and vanilla
Mouthfeel: Silky
Finish: Tart fruit, cinnamon and oak

Score: 79.10


Reveal & Result

L: Green River Single Barrel (#22)
FF: Chattanooga Experimental Single Barrel (#43)

Winner: Green River Single Barrel
➡️ Advances to Round 2

Post-Matchup Thoughts

Not the cleanest matchup of the round. Both had rough edges. In the end, L’s structure and sweetness outweighed FF’s fruit-forward profile.

What decided it:
Better balance despite early ethanol notes.


🔀 Second-Round Matchups Created

High West Chardonnay Cask (#59)
vs.
Jack Daniel’s Oloroso Cask (#27)

Woodford Reserve Double Oaked (#54)
vs.
Green River Single Barrel (#22)


🏁 Closing the First Round

Round 1 is complete.

A few themes emerged:

  • Texture consistently separated winners.

  • Dessert-forward profiles performed extremely well.

  • High proof alone did not guarantee advancement.

  • Some familiar names are already gone.

Now the real fun begins.

Round 2 is where reputations get tested. I’ll see you on Tuesday for the start of Round Two.

Copyright © 2026 Doug DeBolt.

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About Douglas Blaine

Capnpen is a writer who was a newspaper and magazine journalist in a previous life. A college journalism major, he now works as an English teacher, but gets his writing fix by blogging about a variety of topics, including politics, religion, movies and television. When he's not working or blogging, Capnpen spends time with his family, plays a little golf (badly) and loves to learn about virtually anything.
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