In 2004, after hosting many informal tournaments and parties, a group of young University of
Illinois alumni, calling themselves the “Drinking Illini” began organizing a bi-annual flip cup
tournament for fellow alumni and friends living in and around the Chicago area every fall and
spring. The tournaments were initially held at U.S. Beer Co in Lincoln Park but eventually the
size of the tournament grew too large and the move was made to Joe's Bar on Weed Street.
The early tournaments were usually around 36 teams, but eventually grew into a 65 team
event. Teams consisted of 4-5 people and uniforms were mandatory, the winning teams
received a team trophy that was passed on to the next winner each tournament.
In 2006, a group of friends calling themselves “Team Monkey” began organizing an annual flip
cup tournament in the Chicago area to raise money for the Cystic Fibrosis Foundation. The
tournament was a round robin style tournament, and all the proceeds were donated to CFF.
Team uniforms were also mandatory, and the winners received different prizes that had been
Eventually, responsibility came calling and many of the original “Team Monkey” and “Drinking
Illini” members started reciting vows, reproducing, and moving out of the city. In 2008, Ann
Flaharty, the leader of “Team Monkey” and Dana Regan, a relative of one of the original
“Drinking Illini”, took over their respective tournaments and combined them into one annual
tournament to be held in the spring, the Team Monkey/ Drinking Illini Annual Flip Cup
The first TMDI Tournament was held in 2008 at Joe's on Weed St, over $2400 was raised with
53 teams playing, with the proceeds split between the Cystic Fibrosis Foundation (Ann’s
charity) and Autism Speaks (Dana’s charity). The following year, 55 teams helped raise over
$2,600 for CFF and Clearbrook, the largest provider of services to people with developmental
disabilities in the Chicagoland area. In 2010, due to time constraints, Dana and Ann brought in
the Associate Board of Clearbrook (of which Dana is a member) to provide assistance in
organizing and running the tournament. In 2012, Ann moved out of state and brought in
another long-time supporter for CFF, Brent Fayhee, to represent CFF. Brent’s annual CFF
fundraiser has now merged with the TMDI tournament, bringing on a ton of new participants
in the TMDI Flip Cup tournament!!!
Since 2008, thanks to our loyal supporters and Joe’s Bar on Weed St, the TMDI tournament
has raised over $20,000 for our Clearbrook and Cystic Fibrosis!