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Transactions listed are from November 1 of previous year to April 1 of the following year.
November 9, 1908
Sold Chet Chadbourne to Indianapolis (American Association).
Sold Ralph Glaze to Indianapolis (American Association).
November 23, 1908
Signed Harry Hooper as a free agent.
December 12, 1908
Traded Lou Criger to the St. Louis Browns. Received Tubby Spencer and $5,000.
February 16, 1909
Sold Gavvy Cravath to the Chicago White Sox.
Traded Cy Young to the Cleveland Naps. Received Charlie Chech, Jack Ryan and $12,500.
June, 1909 (Standings)
Signed Ray Collins as a free agent.
June 29, 1909 (Standings)
Purchased William Matthews from Trenton (Tri-State).
July, 1909 (Standings)
Purchased Larry Pape from Milwaukee (American Association). (Date given is approximate. Exact date is uncertain.)
July 17, 1909 (Standings)
Purchased Steve Yerkes and Fred Anderson from Wilson (Eastern Carolina) for $1,200.
July 23, 1909 (Standings)
Purchased Hugh Bradley from Worcester (New England).
July 26, 1909 (Standings)
Traded Charlie Chech, Jack Ryan and cash to St Paul (American Association). Received Charley Hall and Ed Karger.
August, 1909 (Standings)
Purchased Frank Barberich from Providence (Eastern). (Date given is approximate. Exact date is uncertain.)
Purchased Paul Howard from Lowell (New England). (Date given is approximate. Exact date is uncertain.)
Purchased Hap Myers from Sacramento (PCL). (Date given is approximate. Exact date is uncertain.)
September, 1909 (Standings)
Drafted Duffy Lewis from Oakland (PCL) in the 1909 rule 5 draft.
September 9, 1909 (Standings)
Traded Doc Gessler to the Washington Senators. Received Charlie Smith.
September 11, 1909 (Standings)
Selected Jack Chesbro off waivers from the New York Highlanders.
January 18, 1910
Harry Wolter selected by the New York Highlanders off waivers for $1,500.