As observed by Mike Cheyne and others in 2014, the rivalry between Matt Jackson and Matt Bollinger was perhaps the greatest ongoing high-level quizbowl rivalry of all time, the "Magic/Bird, Stone Cold/Rock" pairing of quizbowl. It is unclear how Seth Teitler and Jerry Vinokurov feel about this assessment.
The first recorded face-off between the two players took place in May 2009, late in their junior year of high school, at the Monroe Academic Tournament (with the fitting acronym MATT), hosted by James Monroe High School in Fredericksburg, VA . Though the score was close to tied at the half, and neither Jackson nor Bollinger were at that point leading their teams in scoring, GDS won the game 505-155.
After a summer of intense study, the two players continued to face off as the leaders of the two best teams in the Washington, D.C. metro area in the 2009-2010 high school season, often meeting in crucial games. Both of them traveled to play solo at the 2010 ACF Winter tournament at NC Wesleyan, splitting their games with each other and otherwise beating all the college teams present except for the VCU and Maryland squads that finished atop the tournament. At both the NAQT Maryland/DC championships and the late-season Maryland tournament, Jackson's GDS team defeated Bollinger's St. Anselm's team in first v. second place matches to take the titles. At the 2010 NSC, Bollinger's St. Anselm's team emerged victorious from the tiebreakers in a 440-420 slugfest with Jackson's Georgetown Day team in the playoffs, which ultimately determined which team took the fourth-place national trophy in the tournament. However, Jackson was the top individual scorer for the event.
Both players had immediate impacts in college, at Yale and UVA respectively, most notably at the 2011 ACF Nationals, where Jackson led his team to victory as the only freshman to ever lead a national championship team in scoring, and Bollinger led a depleted UVa into the top superplayoff bracket, upsetting multiple teams who had finished in the top 10 of NAQT nationals the week before. Jackson also picked up a DII national title at that year's ICT, while Bollinger finished just a third of a tossup per game behind Chris Ray for top scorer in DI.
In 2012, Bollinger's UVA team won the ICT, and Jackson rejoined the DI squad, which he led to a third-place finish.
The two teams met in the finals of ACF Nationals, which Jackson's Yale team won on the final tossup.
2013 saw the second national finals pairing of the two teams, as Yale defeated UVA in the finals of ICT 390-350 following Jackson's power on the final tossup of the game. Yale also made their third straight run to the ACF Nationals finals.
In 2014, the teams met for the third time in a final, as Bollinger's Virginia team reversed the 2013 result and defeated Jackson's Yale team when Bollinger answered the final tossup of the ICT final. The undergraduate rivalry concluded with Virginia's victory at 2014 ACF Nationals. While no final with Yale was required (UVA cleared the field with no losses and Yale had two), the tournament fittingly ended with Yale in second place, the fourth 1st-2nd pairing of the teams, with two titles for each, in a three-year period. This result was repeated at the 2014 Chicago Open, where Bollinger was again top scorer, and Jackson was third; Bollinger's team went undefeated to win the event, while Jackson's again got second.
The main division of the 2011 ICT, a year in which Jackson elected to play Division II, was the only national tournament of the eight held during Jackson and Bollinger's undergraduate years that did not feature either player in the final, and one of only two that neither player won. Matt Jackson's worst finish at ACF Nationals in his entire undergraduate career was second place.
- As calculated by Bollinger, his career record against Jackson with their school's teams is 16 wins, 14 losses.
- Bollinger and Jackson both traveled to Winter 2010 in a car hilariously driven by Chris Ray, which inaugurated years of Waffle House jokes.
- The rivalry split the loyalties of Jacob Wasserman, who played with Bollinger at St. Anselm's until 2010 and with Jackson at Yale from 2012 to 2014.
- Bollinger and Jackson played VCU Sunday 2010 and CO History Doubles 2012 on the same team. When Bollinger head-edited Chicago Open 2013, Jackson freelanced over 50 questions, including most of the tournament's philosophy, and provided much-needed logistical assistance.
- Matt Weiner's dream to engineer an "all-Matt team" at Chicago Open has remained sadly unfulfilled. However, an alliance of Jackson and Bollinger (with Auroni Gupta and Tommy Casalaspi) did win the 2015 Chicago Open, with Jackson and Bollinger as the tournament's second- and third-place individuals.
- The last tossup in the 2013 ICT Division I final between a Jackson-led Yale and a Bollinger-led Virginia was on Kazakhstan. Jackson got the tossup, and won the championship for Yale. Two years later, when Jackson won his Jeopardy! Tournament of Champions semifinal, the Final Jeopardy answer was "Kazakhstan" and Jackson wrote (hi Matt B.) after his (correct) answer.