Regular Play[]
He is recognized for his buzzer speed and for quickly moving onto the next clue after giving a correct response. In his fourth game, when Jackson said "Boom!" after correctly answering a Daily Double, fans and media quickly proclaimed the exclamation his signature catchphrase, but he never repeated it.
Unlike the traditional $200 down method and the $1,000 up method used by James Holzhauer and Matt Amodio, Jackson tended to select clues from the $600 mark, as clues around this range are more likely to be Daily Doubles.
For his third through eleventh appearances, Jackson held up a number of fingers corresponding to his number of wins coming into that show in his introduction. (In his tenth game, one of his competitors, Erik Latshaw, held up a "0" with his fingers, in imitation of Jackson.)
| Game No. | Air Date | Final score | Cumulative Winnings | Notes |
|---|---|---|---|---|
| 1 | September 25, 2015 | $21,200 | $21,200 | |
| 2 | September 28, 2015 | $30,000 | $51,200 | |
| 3 | September 29, 2015 | $30,000 | $81,200 | |
| 4 | September 30, 2015 | $24,800 | $106,000 | |
| 5 | October 1, 2015 | $34,401 | $140,401 | WE ASKED: Quarterback Aaron Rodgers. Matt's first game without a runaway. |
| 6 | October 2, 2015 | $26,000 | $166,401 | |
| 7 | October 5, 2015 | $24,200 | $190,601 | |
| 8 | October 6, 2015 | $40,009 | $230,610 | |
| 9 | October 7, 2015 | $18,801 | $249,411 | Matt's second game without a runaway. |
| 10 | October 8, 2015 | $40,000 | $289,411 | |
| 11 | October 9, 2015 | $50,000 | $339,411 | |
| 12 | October 12, 2015 | $51,000 | $390,411 | |
| 13 | October 13, 2015 | $21,201 | $411,612 | |
| 14 | October 14, 2015 | $399 | $413,612 | Matt's third game without a runaway. Michael Baker ends his streak. |
Tournament of Champions[]
In the third quarterfinal game, he faced 5-day champion John Schultz and 2015 Teachers Tournament winner Jennifer Giles. He gave 29 correct responses (including one DD) and no wrong responses. Final Jeopardy was a Triple Stumper. Matt's small wager advanced him to the semifinals. John's $15,000 got him a wildcard, while Jennifer was eliminated with $3,800.
In the semifinal game, he faced 5-day champion Andrew Haringer and 4-day champion Catherine Hardee. He gave twenty-three correct respones (including one DD) and no wrong responses and entered Final with a lock game. He and Catherine got Final right and wagered nothing. Matt advanced to the finals.
In the finals, he faced 6-day champions Kerry Greene and Alex Jacob. In game one, he gave seventeen correct responses (including one DD) and two wrong responses. Final Jeopardy was a Triple Stumper. He wagered $11,600 and finished game one in third place. In game two, he gave twenty-one right responses and three wrong responses (including one DD). Kerry was the only correct respondent but Alex's runaway made him the $250,000 champion. He finished with $100,000 for first runner-up.
All-Star Games[]
He was one of eighteen champions selected to take part in the show’s first ever team tournament. He was selected for Ken Jennings’ team, along with 2012 College Championship winner Monica Thieu, who herself defeated Jennings on 500 Questions. Team Ken won their initial match, After that, they finished runner-up behind Team Brad and shared $300,000.
His show winnings total $613,612; he is currently in 9th place for most money won on the show overall.
Jeopardy! Invitational Tournament[]
In the third quarterfinal game, he faced 2014 College Champion and Tournament of Champions semifinalist Terry O'Shea and 6-day champion, 2017 Tournament of Champions first runner-up and 2019 All-Star Games second runner-up Alan Lin. He gave 26 correct responses (including two DDs) and one wrong response. He and Alan got Final right. He entered Final with a runaway, wagered $121 and advanced to the semifinals.
In the third semifinal game, he faced 2021 Professors Tournament winner, 2022 Tournament of Champions second runner-up and 2023 Masters sixth place Sam Buttrey and 1-day champion Victoria Groce. He gave sixteen correct responses and only one response. He was the only player who did not get it right and took home $10,000.