I have it recorded on our DVR satellite receiver. I just checked that scene and it does say 10/20/99 for the date under the comment about the Honor Roll.
Could be they used an old report card because it helped illustrate the point that he does well in school, but it also wouldn't be that far off. If the movie was released in 2003, they probably spent a couple of years filming it and then there was probably time spent editing it and preparing it for release.
Did you notice how much Anna's hairstyle changed throughout the film? There was obviously a lengthy time lapse. I don't think this is unusual for documentaries, for years to be spent filming them.
"You can't tell me nothin' if you ain't had an 8-track." -Sinbad
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