January 14, 1959: Traded Si Green to the St. Louis Hawks for Med Park and Jack Stephens.
March 31, 1959: Traded Archie Dees and a 1959 2nd round draft pick (Tom Robitaille was later selected) to the Detroit Pistons for Phil Jordon.
March 31, 1959: Selected Bob Boozer (1st round, 1st pick) in the 1959 NBA Draft.
August 22, 1959: Traded Johnny McCarthy to the St. Louis Hawks for Whitey Bell, Win Wilfong and Tom Hemans.
January 31, 1960: Traded Dave Piontek to the St. Louis Hawks for Dave Gambee and Hub Reed.
April 11, 1960: Selected Oscar Robertson (1st round, 1st pick), Jay Arnette (2nd round, 9th pick), Ralph Davis (3rd round, 17th pick) and Sam Stith (8th round, 56th pick) in the 1960 NBA Draft.
April 15, 1960: Sold Dave Gambee to the St. Louis Hawks.
April 25, 1960: Fired Tom Marshall as Head Coach.
April 25, 1960: Hired Charles Wolf as Head Coach.
November 14, 1960: Purchased Mike Farmer from the New York Knicks.
November 28, 1960: Sold Phil Rollins to the St. Louis Hawks.
January 18, 1961: Sold Phil Jordon to the New York Knicks.
March 27, 1961: Selected Larry Siegfried (1st round, 3rd pick), Bob Wiesenhahn (2nd round, 11th pick), Bevo Nordmann (3rd round, 25th pick), Dave Zeller (7th round, 61st pick) and George Patterson (12th round, 100th pick) in the 1961 NBA Draft.
May 16, 1961: Purchased Sam Stith from the New York Knicks.
May 16, 1961: Sold Sam Stith to the New York Knicks.
June 25, 1961: Traded a future draft pick to the St. Louis Hawks for Joe Buckhalter.
August, 1961: Sold Mike Farmer to the St. Louis Hawks. Farmer played in the ABL in between.
March 26, 1962: Selected Jerry Lucas (1st round, 6th pick) and Bud Olsen (2nd round, 15th pick) in the 1962 NBA Draft.
July 13, 1962: Traded Larry Staverman to the Chicago Zephyrs for Dave Piontek. Staverman played in the ABL in between.
September 14, 1962: Traded a 1963 2nd round draft pick (Jim King was later selected) to the Los Angeles Lakers for Tom Hawkins.
October 12, 1962: Sold Bevo Nordmann to the St. Louis Hawks.
April 30, 1963: Selected Tom Thacker (1st round, 5th pick) in the 1963 NBA Draft.
June 18, 1963: Hired Jack McMahon as Head Coach.
September 24, 1963: Sold Hub Reed to the Los Angeles Lakers.
December 16, 1963: As part of a 3-team trade, the Cincinnati Royals traded Bob Boozer to the New York Knicks; the Detroit Pistons traded Larry Staverman to the Cincinnati Royals; the Detroit Pistons traded Johnny Egan to the New York Knicks; and the New York Knicks traded Donnie Butcher and Bob Duffy to the Detroit Pistons.
May 4, 1964: Selected George Wilson (1st round, 8th pick), Steve Courtin (3rd round, 26th pick) and Happy Hairston (4th round, 35th pick) in the 1964 NBA Draft.
August 26, 1964: Sold Steve Courtin to the Baltimore Bullets.
May 6, 1965: Selected Nate Bowman (1st round, 9th pick), Flynn Robinson (2nd round, 18th pick), Jon McGlocklin (3rd round, 27th pick), Bob Love (4th round, 36th pick) and Jim Fox (8th round, 70th pick) in the 1965 NBA Draft.
October 20, 1965: Traded Bud Olsen and cash to the San Francisco Warriors for Connie Dierking and Art Heyman.
May 11, 1966: Selected Walt Wesley (1st round, 6th pick), Jim Ware (3rd round, 26th pick) and Freddie Lewis (10th round, 88th pick) in the 1966 NBA Draft.
September 14, 1966: Sold Tom Hawkins to the Los Angeles Lakers.
September 15, 1966: Traded Wayne Embry to the Boston Celtics for a 1967 3rd round draft pick (Sam Smith was later selected).
September 23, 1966: Signed Bill Dinwiddie as a free agent.
November 25, 1966: Traded George Wilson to the Chicago Bulls for Len Chappell.
May 2, 1967: Hired Ed Jucker as Head Coach.
May 3, 1967: Selected Gary Gray (3rd round, 26th pick) in the 1967 NBA Draft.
October 20, 1967: Traded Flynn Robinson, a 1968 2nd round draft pick (Ron Dunlap was later selected) and a 1969 2nd round draft pick (Johnny Baum was later selected) to the Chicago Bulls for Guy Rodgers.
November 27, 1967: Traded Len Chappell to the Detroit Pistons for a 1968 3rd round draft pick (Fred Foster was later selected).
February 1, 1968: Traded Jim Fox and Happy Hairston to the Detroit Pistons for John Tresvant and Tom Van Arsdale.
June 4, 1968: Selected Zaid Abdul-Aziz (1st round, 5th pick), Pat Frink (3rd round, 27th pick) and Fred Foster (3rd round, 28th pick) in the 1968 NBA Draft.
January 31, 1969: Traded Zaid Abdul-Aziz and cash to the Milwaukee Bucks for Fred Hetzel.
February 1, 1969: Traded John Tresvant to the Seattle SuperSonics for Al Tucker.