For the entire 1990s, it was indisputably the most prestigious invitational title, and even until 2002 or so it drew a 64-team field, equal in size to the NAQT ICT and bigger than any other event. It nonetheless featured a reliably annual flare-up of either terrible questions, trainwreck logistics, scandalous protest resolution, or some combination of those things. From 2003 to 2006 the tournament grew smaller and smaller, and instead of being an interesting chance to play a variety of nationwide teams on bad questions, it was just a regular local tournament with bad questions. This trend in question quality reversed from 2007 onward, and Penn Bowl now draws several teams from further north and south.
Penn Bowl used to be a two day tournament. In the years of 64 or 68 teams, about six rounds were played on Friday night and the balance on Saturday. The field was split into four groups and played a round-robin. (This took at least 17 rounds because teams couldn't play their own packet.) The top four teams in each bracket advanced to a single-elimination playoff.
The tournament was famous for its delays. (Indeed, one joke called it "Penn-ding" Bowl.) Teams would show up late on Friday night, and again on Saturday morning. In 2001, the tournament stopped for an hour while a new packet was assembled due to the wrong set of questions being read. Also, the need for thirty moderators often placed inexperienced players into the role.
The tournament was on the clock until 2002. Subsequently, the tournament went untimed but maintained NAQT-ish questions in style and length for a few years. The tournament is now mACF in style and gameplay, and played over one day.
The 2005 Penn Bowl was held in spite of an impending snow storm. As the day progressed, the storm got worse and stranded many teams including Maryland in Philadelphia for the night.
From 2007 to 2009, Matt Weiner was the chief editor for Penn Bowl. This move was widely praised for bringing a marked increase in quality of the questions in the tournament.
Since arriving at Penn in 2010, Eric Mukherjee has overseen the tournament, with the exception of the 2011 iteration, in which several non-Eric Penn people oversaw a Penn Bowl of significantly greater length and difficulty (and ironically subtitled the tournament "Written Entirely by Eric Mukherjee"). Logistics generally improved, with the exception of the 2012 iteration (see below), with the event generally being well-received, if not slightly above its difficulty targets.
|Penn Bowl||Date||Champion||Second||Editor(s)||Field size||Notes||Stats||Packets|
|Penn Bowl I||February 2-3, 1991||Princeton||Penn State||31||Some info||Packets|
|Penn Bowl II||January 1992||Chicago||MIT||Packets|
|Penn Bowl III||January 1993||Vanderbilt||Chicago||Packets|
|Penn Bowl IV||January 28-29, 1994||Georgia Tech||Chicago||Pat Matthews||44||More teams were expected, but a snowstorm reduced the field.||Packets|
|Penn Bowl V||January 27-28, 1995||Chicago||Maryland||Pat Matthews||64||Packets|
|Penn Bowl VI||January 27-28, 1996||Michigan||Maryland||Pat Matthews||64||Often called the best of all the old-style tournaments (College Bowl-style questions and rules, very large field) by old people. Some info||Packets|
|Penn Bowl VII||January 24-25, 1998||Chicago||Vanderbilt||Jason Arvey||64||Penn Bowl was not held in 1997 so that Penn could host the first NAQT ICT in its traditional place.||Packets|
|Penn Bowl VIII||January 29-30, 1999||Chicago||South Carolina||Mario Lucero||64||Some info||Packets|
|Penn Bowl IX||January 22-23, 2000||Yale||Cornell||Penn team||Featured three of the top four seeds losing in the first playoff round on a packet with a lot of food-related trash tossups.|
|Penn Bowl X||January 26-27, 2001||Michigan||Princeton||Samer Ismail||Packets|
|Penn Bowl XI||January 25-26, 2002||Princeton||Virginia||Samer Ismail||Packets|
|Penn Bowl XII||January 24-25, 2003||Michigan||Berkeley||Samer Ismail||58|
|Penn Bowl XIII||January 23-24, 2004||Yale||Michigan||Samer Ismail||Featured David Isaacson whining his way into a victory via the "nobody held a gun to their heads" incident||Packets|
|Penn Bowl XIV||January 22, 2005||Florida||Rochester||Nobody||Snow!||Stats||Packets|
|Penn Bowl XV||January 2006||North Carolina||Maryland||Charlie Steinhice||Packets were a Sword Bowl mirror. This was a bad idea.||Packets|
|Penn Bowl XVI||January 20, 2007||Brown||Chicago||Matt Weiner, Eric Kwartler, and Noah Rahman||21||Early expiration of room reservations led to the last few rounds not being played, meaning the first round robin could not be completed, and many teams did not get a chance to play each other||Partial stats||Packets|
|Penn Bowl XVII||January 26, 2008||Maryland||Vanderbilt||Matt Weiner and Billy Beyer||22||Stats||Packets|
|Penn Bowl XVIII||January 24, 2009||Chicago A||Brown||Matt Weiner, Mehdi Razvi, and Mike Bentley||24||Stats (Midwest mirror stats, Northwest mirror stats, Southeast mirror stats)||Packets|
|Penn Bowl XIX||January 25, 2010||Harvard A||Brown A||Mehdi Razvi, Sid Chandrasekar, Chris White, and Eric Mukherjee||25||Prelim stats||Packets|
|Penn Bowl XX||February 12, 2011||UVA||Maryland||Mehdi Razvi, Dominic Machado, Ming Lin, and James Lasker||18||Stats||Packets|
|Penn Bowl XXI||January 28, 2012||UVA||Yale||Eric Mukherjee, James Lasker, Saajid Moyen, Patrick Liao||18||The latter rounds were written during the tournament itself. Citing exhaustion, writing stopped with packet 13 (Editor's 10), which would not have been sufficient to complete an advantaged final if Yale had won game one (thankfully, they didn't). Succeeded by the final, and exponentially more disastrous, incarnation of Penn Bowl Trash.||Stats||Packets|
|not held||February 2, 2013||Mirror of VCU Closed held in its place|
|Penn Bowl XXII||October 19, 2013||UVA||Columbia A||Eric Mukherjee, Saajid Moyen, Patrick Liao||24||Stats||Packets|
|Penn Bowl XXIII (not officially numbered)||October 18, 2014||UVA||Maryland A||Eric Mukherjee, Rob Carson, Patrick Liao, Will Alston||27||No major issues; finished 13 rounds for all teams by 6 PM and the finals by 7||Stats||Packets|
|Penn Bowl XXIV (not officially numbered)||October 24, 2015||Maryland A||Columbia A||Eric Mukherjee, Rob Carson, Patrick Liao, Ike Jose, Eddie Kim||38||No major issues; finished 12 rounds for all teams by 6 PM and the finals by 7||Stats||Packets|
|Penn Bowl XXV||October 22, 2016||Maryland A||Princeton||Eric Mukherjee, Ike Jose, Will Alston, Patrick Liao, Ankit Aggarwal, Chris Chiego||28||No major issues; finished 12 rounds for all teams by 6 PM and the finals by 7||Stats||Packets|
|Penn Bowl XXVI||October 21, 2017||Columbia A||Virginia A||Jaimie Carlson, Jason Zhou, Jordan Brownstein, and Eric Mukherjee||30||No major issues; finished 13 rounds for all teams by 6 PM and the finals by 7||Stats||Packets|
|Penn Bowl XXVII||October 20, 2018||Yale A||Maryland A||Eric Mukherjee, Jordan Brownstein, JinAh Kim, Jaimie Carlson, and Samir Khan||38||Stats||Packets|