These are the first references I can find to sports teams at West Roxbury - later Jamaica Plain - high school. Baseball had been popular for decades by 1901, but apparently high school sports in Boston didn't take off until the dates cited below. It seems as if West Roxbury high was a late-comer to organized teams, but that may have been from a lack of boys. Many boys went to schools like Boston English, which didn't accept girls, and thus funneled off boys from the district schools like West Roxbury and the rest of this new league. All league games were played at Franklin Field in Dorchester, which had been created to keep ballplayers out of Franklin Park.
Surprisingly, West Roxbury high fielded a football team eight years earlier than baseball, and they gave Dedham high a good thrashing.
Boston Daily Globe December 1, 1893
West Roxbury High 12, Dedham High 0.
Dedham, Nov 30 -- About 600 spectators saw the West Roxbury high school team defeat the Dedham high school eleven in a football game on the grounds of the West Roxbury athletic association at Highland today, and by their victory win the silver cup offered by Edward F. Draper of Boston. The Dedham eleven was clearly outclassed as the weight, and, apparently, as to science. The features of the game were the rushes of the West Roxbury eleven; J.D. French's end plays,, center rushes and tackling; the end plays of A.C. Whittemore, Lewis, Conant, Peterson and Easterbrook, and the tackling of Clark, A. French, Meehan, Lewis, Zuner, Currier, A.C. Whittemore, Wight, Chute, Easterbrook, S.R. Williams and Collins. Score, West Roxbury high school 12; Dedham high school 0.
Boston Daily Globe March 20, 1901
Makeup of New Highland Baseball League.
Organization Effected and a Schedule Arranged.
Great Rivalry Exists Among Its Members.
A new interscholastic baseball league has been formed by Roxbury high school, East Boston high, Charlestown high, Brighton high and West Roxbury high, which will put no less than 16 schools in the various championship series this spring.
The new association will be known as the Highland interscholastic baseball league, and with the preparatory league, which comprises Hopkinson, Cambridge Latin, Boston Latin, Brookline high and Newton high, the interscholastic league, which comprises English high, Cambridge high and Somerville high, and interpreparatory league, which comprises Milton academy, Nobles and Greenough, Volkman and Roxbury Latin, much interest and enthusiasm are promised among the schoolboys.
None of the schools in the Highland league are, or have ever been, members of the Boston interscholastic league, although Roxbury high has been anxious to get into it.
The five teams constituting the Highland league are members of the Highland battalion of the Boston school regiment, and in consequence much rivalry exists among them. Roxbury high has been represented by a fairly strong team for the past six or eight years, but to the other schools little attention has been drawn. Brighton high has shown much interest in athletics during the last year, and there is every indication that the ball team will be as successful as was last fall's football eleven.
Charlestown high, West Roxbury high and East Boston high have a large number of candidates out for their respective teams, and every effort will be made by these schools to get out strong aggregations.
The schools have contributed money for a magnificent silver loving cup, the design for which has been accepted already. This will be offered as the championship emblem, and the school winning it four times will become the permanent holder.
At a recent meeting of the delegates of these schools the following officers were elected: Richie, Charlestown high, pres: McDevitt, Brighton high, vice pres; William A. McCann, Roxbury high, sec; and Barrows of Charlestown, treas. The schedule adopted was as follows.
[Each team played the other twice, all games being played at Franklin Field.]