Wait 'til This Year (2004)
Wait 'til This Year is a reality-type docu-drama film which follows a Boston Red Sox fan during the 2004 baseball season, when the team ended their famous losing streak by winning the World Series. The film was aired on New England Sports Network (NESN) and then released on DVD afterward. Monika Lahiri starred (as the "character" Monika) and produced the film, which combines reality, documentary and scripted scenes when following the events from the perspective of Monika.
More at Wikipedia.