1808

• HARRISON GRAY OTIS (FUTURE US SENATOR AND BOSTON MAYOR) ACQUIRES STRAWBERRY HILL PROPERTY 

• OTIS HIRES US CAPITAL ARCHITECT, CHARLES BULFINCH TO REDESIGN C.1715 HOME INTO COUNTRY ESTATE WHICH HE NAMES "OAKLEIGH"

1825

OTIS SELLS PROPERTY TO SUCCESSFUL IMPORT MERCHANT WILLIAM PRATT

1895

CAMBRIDGE GOLF CLUB ESTABLISHED AT MOUNT AUBURN AND SCHOOL STREETS

1896

MEMBER JOSEPH GILBERT THORP PLACES 2ND IN US AMATEUR

1897

STRAWBERRY HILL PROPERTY ACQUIRED FROM PRATT FAMILY BY CLUB MEMBERS

1898

• AFTER EXTENSIVE RENOVATIONS TO OLD MANSION, CLUB MOVES TO STRAWBERRY HILL

• CAMBRIDGE GOLF AND COUNTRY CLUB INCORPORATED

•  WILLIE CAMPBELL lays out 1^st 18 HOLE GOLF COURSE IN MASSACHUSETTS AT CAMBRIDGE GOLF AND COUNTRY CLUB

• CAMBRIDGE GOLF AND COUNTRY CLUB CHANGES NAME  TO THE OAKLEY COUNTRY CLUB

• OAKLEY GROUNDS COMMITTEE MEMBER, ROBERT W. WILLSON, RECRUITS 25 YEAR OLD, DONALD J. ROSS IN DORNOCH SCOTLAND

1899

ROSS ARRIVES AT OAKLEY TO FILL MANY ROLES - MOST IMPORTANTLY THE 11 YEARS HE SPENT ON STAFF DESIGNING, THEN TWEAKING HIS FIRST GOLF COURSE

1900

• WOMANS GOLF ASSOCIATION OF MASSACHUSETTS FORMED WITH OAKLEY, CONCORD, BRAE BURN AND TCC

• 1ST WGAM CHAMPIONSHIP HELD AT OAKLEY

• OAKLEY IRRIGATES GREENS

• ALEC ROSS IS RECRUITED FROM ROYAL DORNOCH BY BROTHER DONALD TO JOIN OAKLEY STAFF AS A PROFESSIONAL. ALEC WOULD GO ON TO WIN 1907 US OPEN.

• HARRY VARDON PLAYS AT OAKLEY

1901

• ROSS SENDS $2,000 TO HIS MOTHER IN DORNOCH. USING THE MONEY TO ADD 2ND FLOOR TO FAMILY HOME, SHE IS SO GRATEFUL, THE HOME IS RENAMED THE "OAKLEY COTTAGE"

• ROSS BEGINS INDOOR GOLF SCHOOL IN OAKLEY SQUASH COURTS

1901-1904

HARVARD STUDENT FRANKLIN D ROOSEVELT PLAYS OAKLEY REGULARLY

1905

• CLUBHOUSE EXPANDED 

• CLUB PRO DONALD ROSS WINS INAUGURAL MASSACHUSETTS OPEN

• PRESIDENT TEDDY ROOSEVELT VISITS OAKLEY

• MEMBER PAULINE MCKAY WINS US AMATEUR CHAMPIONSHIP

1906

MEMBER PAULINE MCKAY IS MEDALIST IN US AMATEUR.

1908

MEMBER KATHERINE HARLEY JACKSON WINS US AMATEUR.

1909

• MEMBER MARY ADAMS WINS WGAM CHAMPIONSHIP

• OAKLEY HOSTS THE MASSACHUSETTS AMATEUR CHAMPIONSHIP

1910

AFTER ACQUIRING THE ADJACENT PAYSON ESTATE, OAKLEY COMPLETES REPLACEMENT OF TWO HOLES. AS DIRECTED IN BOARD MINUTES, THE NEW HOLES ARE LAID OUT ACCORDING TO PLANS PREVIOUSLY DESIGNED BY MR. DONALD J. ROSS. THE OAKLEY LAYOUT HAS REMAINED UNCHANGED EVER SINCE.

1912

• CLUB HOUSE EXPANDED TO 3 STORIES

• OAKLEY HOSTS MASSACHUSETTS OPEN, WHICH IS WON BY FORMER PRO ALEC ROSS

1914

• MEMBER KATHERINE HARLEY JACKSON WINS HER 2ND US AMATEUR

• OAKLEY HOSTS INAUGURAL MASSACHUSETTS JUNIOR AMATEUR, WON BY RAYMOND QUIMET, YOUNGER BROTHER OF FRANCIS

1919

OAKLEY PRO, MIKE BRADY FINISHES 2ND IN US OPEN

1923

• BOBBY JONES PLAYS OAKLEY REGULARLY AS HARVARD GOLF TEAM STUDENT / COACH.

1932

MEMBER EDITH BAKER WINS HER FIFTH MASSACHUSETTS AMATEUR CHAMPIONSHIP

1934

• NEW ENGLAND INTERCOLLEGIATE GOLF CHAMPIONSHIP BEGINS TWO DECADES AT OAKLEY PLAYING FOR THE "OAKLEY CUP" WHICH CONTINUES TO BE PRESENTED TO ANNUAL WINNER

• MEMBER ROSAMUND VAHEY WINS HER
3RD MASSACHUSETTS AMATEUR CHAMPIONSHIP

1937

JOHN F. KENNEDY PLAYS OAKLEY REGULARLY AS MEMBER OF HARVARD FRESHMAN GOLF TEAM

1942

US ARMY INSTALLS ANTI-AIRCRAFT BATTERY ON 5TH HOLE HILL AS PART OF WATERTOWN ARSENAL DEFENSE.

1948

50TH CLUB ANNIVERSARY CELEBRATED WITH FORMAL BALL ATTENDED BY  MASSACHUSETTS GOVENOR  ROBERT F. BRADFORD

1956

MEMBER FRED WRIGHT WINS US SENIOR AMATEUR CHAMPIONSHIP – ADDING TO HIS RECORD 7 MASSACHUSETTS AMATEUR TITLES

1960

OAKLEY POOL COMPLETED

1962

FIRE DESTROYES BULFINCH CLUBHOUSE

1963

NEW CLUBHOUSE OPENS

1965

Oakley irrigates fairways

1967

Golf Carts Arrive

1968

OAKLEY PRESIDENT MIKE OHANIAN
WINS MA AMATEUR CHAMPIONSHIP

1973

75th Club Anniversary celebrated

1983

New Proshop & Maintenance building opens

1987

OAKLEY HOSTS MASSACHUSETTS SENIOR AMATEUR CHAMPIONSHIP

1993

CAROLYN BODAY WINS RECORD 9TH CLUB CHAMPIONSHIP

1994

DR. DANIEL SHEA IRRIGATION POND COMPLETED

1998

• NEW CLUBHOUSE OPENS

• DONALD J ROSS LIBRARY DEDICATED

• OAKLEY CENTENNIAL  CELEBRATED WITH FORMAL BALL ATTENDED BY MS. LILLIAN ROSS PIPPITT, DONALD ROSS' ONLY CHILD

2000

OAKLEY HOSTS 100TH WGAM CHAMPIONSHIP

2012

OAKLEY HOSTS MASSACHUSETTS JUNIOR AMATEUR FOR A RECORD TYING 6TH TIME

2013

NEW FITNESS CENTER OPENS

2014

NEW GOLF PRACTICE AREA INSTALLED

2015

ROBERT MALCOLM WINS RECORD 22nd CLUB CHAMPIONSHIP

2017

OAKLEY HOSTS MASSACHUSETTS SENIOR AMATEUR CHAMPIONSHIP

2019

CLUBHOUSE EXPANSION AND RENOVATIONS COMPLETED