| Year | Class | League | Record | Event |
| 1930-1940 | ?? | ?? | ?? | Red Sox amateur baseball team formed |
| 1940-1962 | ?? | ?? | ?? | Red Sox joined Vermillion Eagles and play semi-pro baseball |
| 1962 | ?? | ?? | ?? | Red Sox reformed amateur baseball team |
| 1963 | ?? | ?? | ?? | ?? |
| 1964 | ?? | ?? | ?? | ?? |
| 1965 | ?? | ?? | ?? | ?? |
| 1966 | ?? | ?? | ?? | ?? |
| 1967 | ?? | ?? | ?? | ?? |
| 1968 | ?? | ?? | ?? | ?? |
| 1969 | ?? | ?? | ?? | ?? |
| 1970 | ?? | ?? | ?? | Kirk Sorensen joined Red Sox after Legion season ended |
| 1971 | Class B | ?? | 8-15 | Did Not Qualify for State Tournament |
| 1972 | Class B | ?? | 1-18 | Did Not Qualify for State Tournament |
| 1973 | Class B | ?? | 12-12 | Did Not Qualify for State Tournament |
| 1974 | None | Northwest Iowa League | 17-10 | Won NW Iowa League Title |
| 1975 | Class B | Northwest Iowa League & South Central League (SD) | ?? | NW Iowa League Title, South Central League Title & 1st Qualification for SD State Tournament |
| 1976 | Class B | South Central League | 27-6 | South Central League Title, District 6 Champions, defeated in semi-finals of State Tournament by Sioux Falls |
| 1977 | Class B | South Central League | ?? | South Central League Title & Did Not Qualify for State Tournament |
| 1978 | Class B | Lewis & Clark League | 20-6 | Did Not Qualify for State Tournament defeated by Yankton Lakers |
| 1979 | Class B | Lewis & Clark League | ?? | Rebuild year - Did Not Qualify for State Tournament Defeated by Yankton Lakers in 3 game series |
| 1980 | Class B | Lewis & Clark League | ?? | .500 season - Did Not Qualify for State Tournament |
| 1981 | Class B | State Line League | 14-7 | Did Not Qualify for State Tournament |
| 1982 | Class B | State Line League | 11-10 | Did Not Qualify for State Tournament |
| 1983 | Class B | State Line League | 12-8 | Did Not Qualify for State Tournament |
| 1984 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in 1st round of State Tournament by Canova |
| 1985 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in 1st round of State Tournament |
| 1986 | Class B | State Line League | 21-4 | State Line League Title, District Title, Ranked # 3 in State Tournament, defeated 1st round of State Tournament by White Lake |
| 1987 | Class B | State Line League | ?? | District Title, defeated 2nd round of State Tournament by Lake Nordon |
| 1988 | Class B | State Line League | ?? | Defeated in 1st round of State Tournament |
| 1989 | Class B | State Line League | ?? | State Line League Title, District Title, defeated 1st round in State Tournament by Tripp |
| 1990 | Class B | State Line League | ?? | Defeated in 1st round of State Tournament |
| 1991 | Class B | State Line League | ?? | District Title, defeated in 3rd game of State Tournament by Claremont |
| 1992 | Class B | State Line League | ?? | State Line League Title, District Title, 2nd Place in State - defeated in Championship game of State Tournament by Madison |
| 1993 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in semi-finals of State Tournament by Canova |
| 1994 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in semi-finals of State Tournament by Dall Rapids PBR |
| 1995 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in semi-finals of State Tournament by Renner/Old Milwaukee |
| 1996 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in Championship Game of State Tournament by Dell Rapids |
| 1997 | Class B | State Line League | ?? | State Line League Title, defeated in 1st round of State Tournament by Canova |
| 1998 | Class B | State Line League | ?? | State Line League Title, defeated in 1st round of State Tournament by Dell Rapids |
| 1999 | Class B | State Line League | 18-8 | State Line League Title, District Title, defeated in semi-finals of State Tournament by Wynot, NE |
| 2000 | Class B | State Line League | ?? | State Line League Title, District Title, defeated in 3rd game (quarter-finals) of State Tournament by Lake Nordon |
| 2001 | Class B | State Line League | 30-8 | State Line League Title, defeated in 2nd game of State Tournament by Dell Rapids PBR |
| 2002 | Class B | State Line League | 26-3 | State Line League Title, District Title, defeated in 2nd game of State Tournament by Redfield |
| 2003 | Class B | State Line League | 30-4 | State Line League Title, District Title, CLASS B STATE CHAMPIONS!! (defeated Freeman 11-0) |
| 2004 | Class B | State Line League | 26-6 | State Line League Title, District Title, REPEAT CLASS B STATE CHAMPIONS!! (defeated Redfield) |
| 2005 | Class A Wood Bats | State Line League | 18-12 | State Line League Title, Did Not Qualify for State Tournament |
| 2006 | Class A Wood Bats | State Line League | 23-6 | State Line League Title, Region Title, CLASS A STATE CHAMPIONS !! (defeated Renner Monarchs 9-8) |
| 2007 | Class A Wood Bats | State Line League | 22-8 | State Line League Title, defeated 2nd game (1st Round) of State Tournament in Yankton by Renner Roadrunners |
| 2008 | Class A Wood Bats | State Line League | 19-5 | State Line League Title, defeated 4th game (2nd Round) of State Tournament in Mitchell by Renner Roadrunners - FINISHED 4TH PLACE |
| 2009 | Class A Wood Bats | State Line League | 15-9 | Lost 2 of 3 games in League Playoffs and did not qualify for State Tournament |