|State Championships||Masonic 1996|
Homewood-Flossmoor is located just South of Chicago. Over time, they probably have been the strongest program in the South Suburbs, winning nine IHSA Sectional Titles and several SICA Conference Titles.
Throughout much of the 1990s, H-F hosted one of the largest tournaments in Illinois, typically occurring in January and attracting over forty teams. The questions were written, and the tournament was run, by Will Oldaker, who is now a member of the IHSSBCA Hall of Fame. Oldaker's teams consistently were among the strongest in the state, playing a full schedule of local tournaments and winning close to ninety percent of their matches.
In the first few years of the 21st Century, the team returned to powerhouse status under Coach Robert Girsch, thanks in large part to the play of Parag Bhayani.
The team, now coached by Michael Sacks, is perhaps the top team in the South Suburbs. They won their IHSA Sectionals in 2006, 2008, 2009, 2013, and 2015. Coach Sacks also revived the Homewood-Flossmoor Invitational for a couple of years and then started hosting IHSSBCA tournaments such as Kickoffs and Turnabouts.
Noted team accomplishments
- IHSA Regional Titles (12): 2002, 04, 05, 06, 08, 09, 10, 12, 13, 14, 15, 16
- IHSA Sectional Titles (12): 1990-93, 95, 97, 2002, 06, 08, 09, 13, 15
IHSSBCA individual awards
The following were honored by the Illinois High School Scholastic Bowl Coaches Association (IHSSBCA) for outstanding play through their All-Sectional/All-State Program. Each sectional comprises roughly 24 geographically concentrated teams, and thus roughly 125 starting players. Through the 2006-07 season, the top ten players were recognized in each sectional, (starting with 2007-08, the number was raised to 15) with teams restricted to no more than two nominations (three nominations starting in 2007-08). There are twenty All-State awards given each year (10 First Team, 10 Second Team) in each of Illinois' two classes.
- 2001-02: Parag Bhayani
- 2003-04: Matt Khan
- 2004-05: Ryan Ferguson
- 2005-06: Joe Houlihan
- 2006-07: Max Willer
- 2007-08: Christopher Izzo, Mike Marszowski, James Shannon
- 2014-15: Michael Gislason
- 2015-16: Michael Gislason, Lily Hamer
- 2016-17: Declan Cawley, Lily Hamer
- 2001-02: Parag Bhayani (1st team)
- 2005-06: Joseph Houlihan (2nd team)
- 2014-15: Michael Gislason (2nd team)
- 2015-16: Michael Gislason (1st team), Lily Hamer (2nd team)
- 2016-17: Lily Hamer (1st team)
Playing for Team Illinois
- Parag Bhayani (2002) -- selected to All-American Team
Despite the loss of player Michael Gislason and a new assistant coach, H-F enjoyed moderate success in the 2016-2017 season, and their accomplishments included being tied for 4th at NAQT state and qualifying for Masonic state for the first time in recent school history. H-F won their conference championships but lost their sectional to rival Sandburg, a team that they had gone 4-2 with throughout the year. Senior Lily Hamer also had the unprecedented-for-H-F distinction of being named to the all-tournament team of every tournament the team attended. The accomplishments of the season were made even more remarkable considering the apathy of the varsity starting lineup- the phrases "Who cares?" and "It's just a game anyway" were heard increasingly often as the long-awaited last tournament of the season neared. Junior Declan Cawley made the All-Sectional team, and distinguished himself as the team mythology and psych player.
2016 NAQT state- H-F tied for fourth place at NAQT state, an improvement on their eighth-place finish at the previous tournament. With sophomore Jimmy Humphrey promoted temporarily to the A team, the team was in good spirits and won two narrow victories over Carbondale. Senior Lily Hamer had an exceptionally good day, powering nearly every Shakespeare question (once, memorably, so early that the moderator thought she had dropped her buzzer), and getting a long-awaited question on the movie Milk first clue. Juniors Declan Cawley (newly promoted to team captain) and Luca Strohmeier, and senior Thomas Simon also put up a good fight, and Luca powered a Simpsons tossup to cement the second win over Carbondale. Jimmy Humphrey was especially lauded for getting one of only a few tossups scored over Stevenson.
Current varsity players
- 1990 IHSA State Championship Tournament
- 1991 IHSA State Championship Tournament
- 1992 IHSA State Championship Tournament
- 1993 IHSA State Championship Tournament
- 1995 IHSA State Championship Tournament
- 1997 IHSA State Championship Tournament
- 2002 IHSA State Championship Tournament
- 2006 IHSA State Championship Tournament
- 2008 IHSA State Championship Tournament
- 2009 IHSA State Championship Tournament
- 2013 IHSA State Championship Tournament
- 2015 IHSA State Championship Tournament