* Last updated at 9:30 am on Sunday, April 21, 2024

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Season summaries include titles won (and the class they were won in), final place in state, final won-lost record, and head coach for all seasons submitted by the school or gathered from IHSA records.

A few titles are missing (complete list of missing titles). Changes and additions to these records may be made by school personnel through the IHSA Schools Center.

Key to titles: D–district, R–regional, S–sectional, U–super-sectional, Q–team qualifier for state finals, P–Chicago Public League champion (only when an automatic qualifier to the state finals).

Pleasant Hill

Baseball

Season Class Titles Place Won Lost Tied Coach
2000-01       6 13   Kevin McKinnon
2001-02       7 15   Kevin McKinnon
2002-03       4 16   Kevin McKinnon
2003-04       3 18   Kevin McKinnon
Coach Total 20 62   4 yr   .244
School Total 20 62   4 yr   .244

Boys Basketball

Season Class Titles Place Won Lost Tied Coach
1926-27   D          
1927-28   D          
1928-29   D   22 6   Coach Elder
1929-30       7 10   Coach Elder
Coach Total 29 16   2 yr   .644
1930-31   D   22 7   Coach Kehart
Coach Total 22 7   1 yr   .759
1931-32       20 8   Coach Hubbell
1932-33       26 4   Coach Hubbell
1933-34       10 8   Coach Hubbell
Coach Total 56 20   3 yr   .737
1934-35       17 5   Coach Bierman
Coach Total 17 5   1 yr   .773
1935-36   D   13 10   Coach Lathrop
Coach Total 13 10   1 yr   .565
1936-37       18 6   Coach Dickinson
1937-38       18 9   Coach Dickinson
Coach Total 36 15   2 yr   .706
1938-39       8 10   Coach Kessinger
Coach Total 8 10   1 yr   .444
1939-40       11 11   Coache Kessinger
Coach Total 11 11   1 yr   .500
1940-41       9 10   Coach Baker & Crosby
Coach Total 9 10   1 yr   .474
1941-42       9 6   Coach Crosby
1942-43       7 8   Coach Crosby
Coach Total 16 14   2 yr   .533
1943-44       9 8   Coach Husted
Coach Total 9 8   1 yr   .529
1944-45       5 10   Coach Book
Coach Total 5 10   1 yr   .333
1945-46       7 14   Coach Folk
1946-47       10 9   Coach Folk
Coach Total 17 23   2 yr   .425
1947-48       5 14   Coach Hungate
1948-49       2 15   Coach Hungate
Coach Total 7 29   2 yr   .194
1949-50       16 8   Coach Spaulding
1950-51       21 6   Coach Spaulding
1951-52       24 2   Coach Spaulding
Coach Total 61 16   3 yr   .792
1952-53       9 15   Coach Evitt
1953-54       10 15   Coach Evitt
1954-55       13 12   Coach Evitt
Coach Total 32 42   3 yr   .432
1955-56   R   20 8   Coach Landers
1956-57       17 7   Coach Landers
Coach Total 37 15   2 yr   .712
1957-58       6 8   Coach Anderson
Coach Total 6 8   1 yr   .429
1958-59       20 8   Coach Hake
1959-60       10 14   Coach Hake
1960-61       5 6   Coach Hake
1961-62       11 12   Coach Hake
Coach Total 46 40   4 yr   .535
1962-63       15 5   Coach Carlton
Coach Total 15 5   1 yr   .750
1963-64   R   26 2   Richard Deckard
1964-65   R   24 4   Richard Deckard
Coach Total 50 6   2 yr   .893
1965-66       21 5   Coach Wes Rayner
1966-67       9 14   Coach Wes Rayner
1967-68       8 17   Coach Wes Rayner
Coach Total 38 36   3 yr   .514
1968-69       1 20   Coach Chuck Orwig
Coach Total 1 20   1 yr   .048
1969-70       1 20   Chuck Orwig
1970-71       6 17   Chuck Orwig
Coach Total 7 37   2 yr   .159
1971-72       12 11   Coach Chuck Orwig
1972-73       2 21   Coach Chuck Orwig
Coach Total 14 32   2 yr   .304
1973-74       1 22   Coach Brown
Coach Total 1 22   1 yr   .043
1974-75       8 16   Jim Herndon
1975-76       10 14   Jim Herndon
1976-77       9 16   Jim Herndon
1977-78       20 7   Jim Herndon
Coach Total 47 53   4 yr   .470
1990-91       25 3   Harry Wagy
1991-92 A R   18 11   Harry Wagy
Coach Total 43 14   2 yr   .754
1995-96       5 19    
Coach Total 5 19   1 yr   .208
1996-97       2 21   Kent Jahn
Coach Total 2 21   1 yr   .087
1997-98       3 19   Larry Mooney
1998-99       15 10   Larry Mooney
Coach Total 18 29   2 yr   .383
1999-00       8 15   Jeff Shireman
2004-05       12 14   Jeff Shireman
Coach Total 20 29   2 yr   .408
2005-06       3 21   Matt Shwienberg
2006-07       3 19   Matt Shwienberg
Coach Total 6 40   2 yr   .130
2007-08       4 19   Ryan Benz
2008-09       1 21   Ryan Benz
Coach Total 5 40   2 yr   .111
2016-17 1A R         Blake Skillman
School Total 709 712   62 yr   .499

Boys Track & Field

Season Class Titles Place Won Lost Tied Coach
1974-75 A D         Coach Chuck Orwig

Football

Season Class Titles Place Won Lost Tied Coach
1963-64       8 0 1 Richard Deckard
1964-65       7 1 1 Richard Deckard
Coach Total 15 1 2 2 yr   .889
1965-66       7 1 1 Wes Rayner
1966-67       3 4 2 Wes Rayner
1967-68       3 5 1 Wes Rayner
1968-69       4 4 1 Wes Rayner
1969-70       5 4   Wes Rayner
1970-71       5 3 1 Wes Rayner
1971-72       4 4   Wes Rayner
1972-73       2 7   Wes Rayner
Coach Total 33 32 6 8 yr   .507
1973-74       2 7   Bryon Brown
Coach Total 2 7   1 yr   .222
1974-75       2 6 1 Wes Rayner
1975-76       3 5   Wes Rayner
Coach Total 5 11 1 2 yr   .324
1976-77       3 6   Don Flowers
1977-78       6 3   Don Flowers
1978-79 1A Q   10 1   Don Flowers
1979-80       4 5   Don Flowers
1980-81       4 5   Don Flowers
Coach Total 27 20   5 yr   .574
1981-82 1A Q   10 2   Steve Goodman
1982-83 1A Q   8 2   Steve Goodman
1983-84       4 5   Steve Goodman
1984-85       2 7   Steve Goodman
Coach Total 24 16   4 yr   .600
1985-86 1A Q   6 4   Don Flowers
1986-87 1A Q         Don Flowers
1987-88       5 4   Don Flowers
1988-89       3 6   Don Flowers
Coach Total 14 14   3 yr   .500
1989-90 1A Q   7 3   Joe Coldwell
1990-91       4 5   Joe Coldwell
1991-92       1 8   Joe Coldwell
Coach Total 12 16   3 yr   .429
1992-93       2 7   Tony Merryman
1993-94       5 4   Tony Merryman
1994-95       0 9   Tony Merryman
1995-96       0 9   Tony Merryman
1996-97       1 8   Tony Merryman
1997-98       5 4   Tony Merryman
1998-99 1A Q   10 2   Tony Merryman
Coach Total 23 43   7 yr   .348
1999-00       0 9   Ron Edwards
2000-01       2 7   Ron Edwards
2001-02       0 9   Ron Edwards
2002-03       2 7   Ron Edwards
2003-04       3 6   Ron Edwards
2004-05       3 6   Ron Edwards
2005-06       0 9   Ron Edwards
2006-07       1 8   Ron Edwards
Coach Total 11 61   8 yr   .153
2007-08       5 4   Mike Giles
2008-09       4 5   Mike Giles
2009-10 1A Q   7 3   Mike Giles
2010-11       4 5   Mike Giles
2011-12       5 4   Mike Giles
2012-13       3 6   Mike Giles
2013-14       4 5   Mike Giles
Coach Total 32 32   7 yr   .500
2014-15       3 6    
Coach Total 3 6   1 yr   .333
2015-16       1 8   Mike Giles
2016-17       2 7   Mike Giles
2017-18 1A Q   5 5   Mike Giles
2018-19       1 8   Mike Giles
2019-20       0 9   Mike Giles
2020-21       0 5   Mike Giles
2021-22       1 8   Mike Giles
2022-23       1 8   Mike Giles
2023-24       1 8   Mike Giles
Coach Total 12 66   9 yr   .154
School Total 213 325 9 60 yr   .389

Softball

Season Class Titles Place Won Lost Tied Coach
2020-21 1A R         Ryan Lowe
2022-23 1A R         Ryan Lowe