Regular Play[]
In 2005, Madden went on Jeopardy! from July 5 until September 19. Over the course of his 19-day run, he won a grand total of $432,400.
| Game No. | Air Date | Final score | Cumulative Winnings | Notes |
|---|---|---|---|---|
| 1 | July 5, 2005 | $16,400 | $16,400 | David's first game without a runaway and first win from second place. |
| 2 | July 6, 2005 | $18,800 | $35,200 | |
| 3 | July 7, 2005 | $34,200 | $69,400 | |
| 4 | July 8, 2005 | $25,000 | $94,400 | |
| 5 | July 11, 2005 | $32,100 | $126,500 | |
| 6 | July 12, 2005 | $29,000 | $155,500 | |
| 7 | July 13, 2005 | $18,000 | $173,500 | |
| 8 | July 14, 2005 | $25,000 | $198,500 | |
| 9 | July 15, 2005 | $18,600 | $217,100 | |
| 10 | July 18, 2005 | $22,000 | $239,100 | |
| 11 | July 19, 2005 | $30,001 | $269,101 | David's second game without a runaway. |
| 12 | July 20, 2005 | $11,000 | $280,101 | David's third game without a runaway and second win from second place. |
| 13 | July 21, 2005 | $25,000 | $305,101 | |
| 14 | July 22, 2005 | $28,200 | $333,001 | Last game of Season 21. |
| 15 | September 12, 2005 | $21,400 | $354,701 | First game of Season 22. David's fourth game without a runaway and third win from second place. |
| 16 | September 13, 2005 | $23,999 | $378,700 | |
| 17 | September 14, 2005 | $13,200 | $391,900 | |
| 18 | September 15, 2005 | $22,000 | $413,900 | |
| 19 | September 16, 2005 | $16,500 | $430,400 | |
| 20 | September 19, 2005 | $13,300 | $432,400 | David's fifth game without a runaway. Victoria Groce ends his streak and Kelly Miyahara of the Clue Crew introduces herself during the closing credits. |
Aftermath[]
- He participated in the 2006 Tournament of Champions show, just one year after his long-running streak. He won the first round match face to Michael Falk (ToC winner) and Bob Mesko but lost to runner-up 4-time champ Bill MacDonald. He took home $10,000 at that time, bringing his grand total to $442,400.
- He was invited to take part in the 2014 Battle of the Decades tournament, but declined due to contractual issues.
- Madden had first watched Jeopardy! with a babysitter when he was 11–12 years old. Madden would get the correct response to more clues than his babysitter. Madden claims to have studied a great deal in preparation for the show, which helped him with the hints. Madden's parents did not realize he was going to be on Jeopardy!until his first game aired.
- He was allowed to participate in the 2019 All-Star Games tournament, becoming a member of Team Brad. He was selected as the 7th pick in the September 2018 draft, becoming a member of Team Brad, led by the all-time US game show winner, Brad Rutter, along with his former Princeton University Quiz Bowl teammate Larissa Kelly, who was the 6th pick in the draft. Team Brad won their first-round match, and in the final match, won the $1,000,000 grand prize, which was split between the three members. After Madden's share of the achievement, his all-time Jeopardy earnings totaled $773,733.
- As of 2022, he was the sixth-highest all-time winner, behind fellow Jeopardy contestants, Brad Rutter, Ken Jennings, James Holzhauer, Matt Amodio, and Amy Schneider.