| Player History |
| 04/11/1962 | Suspended 10 games after ejection following a brawl. |
| 07/01/1962 | Was selected to the 1962 ORB2 All-Star Game. |
| 08/17/1962 | Injured (strained back muscle), out for 8 weeks. |
| 11/01/1962 | Received a 1-year contract worth a total of $296,880 through arbitration. |
| 01/01/1963 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 7 (4). |
| 04/13/1963 | Signed a 2-year contract extension worth a total of $1,305,000 with the Washington Senators organization. |
| 04/22/1963 | Pitches a 3-hit shutout against the Los Angeles Angels with 6 strikeouts and 1 BB allowed! |
| 09/06/1963 | Pitches a 3-hit shutout against the Cleveland Indians with 4 strikeouts and 1 BB allowed! |
| 01/01/1964 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 7 (4). |
| 07/13/1964 | Pitches a 3-hit shutout against the Boston Red Sox with 7 strikeouts and 0 BB allowed! |
| 01/01/1965 | OSA scouting updated ratings (potential): Stuff: 3 (1); Movement: 8 (4); Control: 7 (3). |
| 03/23/1965 | Injured (finger blister), day-to-day for 1-2 weeks. |
| 05/15/1965 | Pitches a 5-hit shutout against the Cleveland Indians with 2 strikeouts and 2 BB allowed! |
| 07/01/1965 | Wins the ORB2 AL Pitcher of the Month Award. |
| 07/01/1965 | Was selected to the 1965 Other Reality Baseball 2 All-Star Game. |
| 07/21/1965 | Signed a 2-year contract extension worth a total of $1,880,400 with the Washington Senators organization. |
| 10/24/1965 | Wins the 1965 ORB2 AL Honus Wagner Fielding Award at P. |
| 01/01/1966 | OSA scouting updated ratings (potential): Stuff: 1 (1); Movement: 8 (4); Control: 5 (3). |
| 06/25/1966 | Pitches a 3-hit shutout against the Hawaii Islanders with 4 strikeouts and 3 BB allowed! |
| 01/01/1967 | OSA scouting updated ratings (potential): Stuff: 1 (1); Movement: 8 (4); Control: 5 (3). |
| 11/15/1967 | Became a free agent. |
| 01/01/1968 | OSA scouting updated ratings (potential): Stuff: 1 (1); Movement: 8 (4); Control: 5 (3). |
| 12/24/1968 | Signed a 0-year minor league contract with the Oakland Athletics organization. |
| 01/01/1969 | OSA scouting updated ratings (potential): Stuff: 1 (1); Movement: 8 (4); Control: 5 (3). |
| 07/28/1969 | Wins the IL KMLL Player of the Week Award. |
| 12/01/1969 | Drafted SP C. Osteen in the 1969 rule 5 draft (Pick 2, Round 1, 2nd overall Pick) by the Chicago (N) Cubs. |
| 01/01/1970 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 8 (4). |
| 04/24/1970 | Signed a 3-year contract extension worth a total of $169,200 with the Chicago (N) Cubs organization. |
| 07/30/1970 | Pitches a 6-hit shutout against the St. Louis Cardinals with 7 strikeouts and 0 BB allowed! |
| 01/01/1971 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 8 (4). |
| 01/01/1972 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 8 (4). |
| 06/23/1972 | Pitches a 3-hit shutout against the Los Angeles Dodgers with 5 strikeouts and 3 BB allowed! |
| 01/01/1973 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 7 (4); Control: 8 (4). |
| 04/15/1973 | Pitches a 6-hit shutout against the Cincinnati Reds with 3 strikeouts and 1 BB allowed! |
| 05/07/1973 | Pitches a 5-hit shutout against the Philadelphia Phillies with 5 strikeouts and 3 BB allowed! |
| 06/03/1973 | Signed a 2-year contract extension worth a total of $180,000 with the Chicago (N) Cubs organization. |
| 09/14/1973 | Injured (mild oblique strain), day-to-day for 1 day. |
| 01/01/1974 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 7 (4); Control: 8 (4). |
| 06/23/1974 | Pitches a 5-hit shutout against the Milwaukee Brewers with 6 strikeouts and 0 BB allowed! |
| 01/01/1975 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 8 (4). |
| 11/25/1975 | Became a free agent. |
| 01/01/1976 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 8 (4). |
| 01/31/1976 | Signed a 3-year contract worth a total of $663,600 with the Atlanta Braves organization. |
| 10/01/1976 | Wins the ORB2 AL Pitcher of the Month Award. |
| 01/01/1977 | OSA scouting updated ratings (potential): Stuff: 4 (2); Movement: 8 (4); Control: 8 (4). |
| 04/12/1977 | Pitches a 2-hit shutout against the San Diego Padres with 3 strikeouts and 1 BB allowed! |