In 1908, the Winchester Hustlers became charter members of the Class D level Blue Grass League during the season.
They were followed by the Richmond Pioneers (36–34), Lawrenceburg (33–35), Shelbyville Millers (32–37) and the Versailles Aristocrats / Winchester Reds (22–47).
With a record of 75–44, Winchester placed first in the six–team league, playing their championship season under manager Newt Horn.
On May 10, 1909, while pitching for the Hustlers, Toney defeated the Lexington Colts in 17 innings, winning 1–0, striking out 19 batters with one walk.
[13] In their third season of play, the 1910 Winchester Hustlers placed third in the final Blue Grass League standings.
[3] In 1911, the Blue Grass League played a split–season schedule, with the winners of each half season meeting in the Finals.
Under managers Courtney McBrair and Bob Spade, the Orphans finished the 1912 season with an overall record of 31–97, placing sixth in the six–team Blue Grass League.
The Lexington Colts (60–65), Maysville Rivermen (82–47), Paris Bourbonites (60–69) and Richmond Pioneers (66–64) all finished ahead of Mt.
It was noted by the Spalding Guide that the Mount Sterling Orphans team "was in poor shape all of the year.