ASHOLOGY™ Cigar Bracket Challenge

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Connecticut Pilot – Tournament Begins November 30, 2026

ASHOLOGY™ Cigar Bracket Challenge

Powered by CigarOfTheYear™

16 cigars · 15 matchups · One champion. Evaluate both cigars (30 pts), then make a fresh prediction each matchup (20 pts if correct). Maximum 820 points. Two different $100 winners per matchup · $4,200 total player prizes.

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GAME DAY STATS
16
Cigars
15
Matchups

Connecticut Pilot Challenge 2026

Coming Up

Upcoming Matchups

Opening Round opens Monday, November 30, 2026 at 10:00 a.m. ET. All times Eastern. Full schedule

Full bracket →

Each matchup has two separate $100 prizes for two different eligible participants. Complete both cigar evaluations and all required matchup submissions before the matchup closes. A participant cannot win both prizes in the same matchup. If only one eligible participant exists, only one $100 prize is awarded. If there are none, no prize is awarded. Prizes are drawn after the matchup closes and eligibility is verified. Official Rules apply.

M01 Upcoming — opens Nov 30, 2026
Alec Bradley Project 40 Natural Robusto
Alec Bradley
VS
Diesel Uncaged Robusto
Diesel
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Nov 30, 2026 – Dec 6, 2026 (Week 1) Closes: Sun, Jan 17, 2027 · 8:00 PM EST (end of Week 7) Opens in 1 month 3 weeks
M02 Upcoming — opens Nov 30, 2026
La Gloria Cubana Intención Gran Robusto
La Gloria Cubana
VS
El Rey del Mundo Oscuro Robusto Larga
El Rey del Mundo
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Dec 7, 2026 – Dec 13, 2026 (Week 2) Closes: Sun, Jan 17, 2027 · 8:00 PM EST (end of Week 7) Opens in 1 month 3 weeks
M05 Upcoming — opens Nov 30, 2026
CAO Brazilia Gol!
CAO
VS
CAO FASA Sombra Toro
CAO
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Dec 14, 2026 – Dec 20, 2026 (Week 3) Closes: Sun, Jan 31, 2027 · 8:00 PM EST (end of Week 9) Opens in 1 month 3 weeks
M06 Upcoming — opens Nov 30, 2026
Macanudo Café Hampton Court
Macanudo
VS
Macanudo Inspirado White Robusto
Macanudo
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Dec 21, 2026 – Dec 27, 2026 (Week 4) Closes: Sun, Jan 31, 2027 · 8:00 PM EST (end of Week 9) Opens in 1 month 3 weeks
M03 Upcoming — opens Nov 30, 2026
Mr. Punch Toro
Mr. Punch
VS
Punch Knuckle Buster Habano Robusto
Punch
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Dec 28, 2026 – Jan 3, 2027 (Week 5) Closes: Sun, Jan 24, 2027 · 8:00 PM EST (end of Week 8) Opens in 1 month 3 weeks
M04 Upcoming — opens Nov 30, 2026
Chillin' Moose Too Robusto
Chillin' Moose
VS
Shady Moose Robusto
Shady Moose
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Jan 4, 2027 – Jan 10, 2027 (Week 6) Closes: Sun, Jan 24, 2027 · 8:00 PM EST (end of Week 8) Opens in 1 month 3 weeks
M07 Upcoming — opens Nov 30, 2026
Hoyo La Amistad Gold Robusto
Hoyo de Monterrey
VS
Excalibur Epicure English Claro
Excalibur
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Jan 11, 2027 – Jan 17, 2027 (Week 7) Closes: Sun, Feb 7, 2027 · 8:00 PM EST (end of Week 10) Opens in 1 month 3 weeks
M08 Upcoming — opens Nov 30, 2026
Partagás Black Label Crystal
Partagás
VS
Don Tomás Clásico Robusto
Don Tomás
Opens: Mon, Nov 30, 2026 · 10:00 AM EST (Week 1) Counter feature: Jan 18, 2027 – Jan 24, 2027 (Week 8) Closes: Sun, Feb 7, 2027 · 8:00 PM EST (end of Week 10) Opens in 1 month 3 weeks

Official Challenge Locations

Smoke Shops in the Fight

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Official Challenge Locations will be listed here as Connecticut shops are approved. Register your store to join the Connecticut Pilot.