Previous cataloging identified the students as being from Alaska and provides a date of 1901 for the image. It also identifies the white man as an Indian agent.
Based on this, this group would be the one that arrived July 11, 1901 from Woody Island, Alaska. The issue of the school newspaper also mentions that a Mr. C. E. Bunnell accompanied the group, so he is the white man in this photo. The female student in the center left is likely Kate Shepherd.
Here is the description from The Red Man and Helper (Vol. 2, No. 3) August 16, 1901:
"Mr. C. E. Bunnell is making a flying trip to the East during vacation. He took with him eleven young people to attend the Carlisle Indian School. Kate Shepherd, Anastatia Perrin [Anastasia Ashouwak], John Lolchesnekoff, Theodore Schclikoff, Sashka Alexander, George Calaktinoff, and Michael Chabitnoy went from the Orphanage; Olsena Sperbaek [Orleana Yakoff], Pariscovia Feoderoff [Friendoff; Fadaoff] and Nikifer Shouchuk, from Wood Island : and Peter Debrowolsky from Kodiak."