$1
Helen won
The winner was Tom Kavanugh
A number of women have won the Jeopardy Tournament of Champions and can be located in the related link. The newest female winner from the Alex Trebek era of Jeopardy was: Celeste DiNucci who won the tournament for Season 24 held in November 2007 Back at the Beginning of the Art Flemming Era they also had female winners including: Phyllis Gallo won the First annual Jeopardy tournament of champions (1964)
I once saw a show where the returning winner had won only a dollar, but do not remember their name or the date of the show.That was also a show were the second and third place winners won more, but they did not earn the chance to come back as the winner did.Another answer: On January 19, 1993, the winner of that episode finished with $1 and the other two contestants both finished with $0.
The first and second games were both won by Watson the IBM computer
It was won by Michael Bilow with a score of $57198, and with that he had a three day total of $96000.
1,000 dollars
Jesse Cuevas, originally from Kansas, won for the 2nd day, adding $27,600 to his winnings.
Scott Ylinen won with a score of $21150, and as of that episode he had a two day total of $43655
Dave Leach from Georgia won Jeopardy on December 29th, 2011, with a total of $15,599; dethroning 9-day champion Jason Keller, who finished in 2nd place.
Raya won although everyone missed the Final Jeopardy
Tom Nissley won final Jeopardy with a wager of $7,001