Jackson-Bollinger rivalry
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.
The two players began facing 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. Each traveled solo to 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 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 D2 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 D1.
In 2012, Bollinger's UVa team won the ICT, and Jackson rejoined the D1 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 on 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 played, the tournament fittingly ended with Yale in second place, the fourth 1-2 pairing of the teams, with two titles for each, in a three-year period.
The main division of the 2011 ICT, in which Jackson played 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. The rivalry has (temporarily?) ended with their graduation, save for a looming showdown at the 2014 Chicago Open.