Kevin Workman's answer is correct, except for one thing: the movie shows David going back alone three times before the final jump:
- The first time is to change Lollapalooza
- the second time is to save the quarterback
- the third time is when Jessie got erased from existence.
We don't know how long he was in the past for with Lollapalooza and the third jump, but he went back alone three times for at least five minutes before the 2004 jump. See also this timeline.