[11] In 1916, two Ford Motor Company executives, advertising head Joseph Mack and chief accountant and first sales manager Norval Hawkins, purchased a parcel of farmland on Maple Road – 15 miles (24 km) northwest of Detroit in Bloomfield Hills.

The clubhouse was the Miller farmhouse on the North side of Maple Road and the old chicken coop served as Hagen's pro shop.

The original structure had accommodations for 48 overnight guests, as it was not uncommon in that era for members to stay at the Club for weeks at a time.

Modern roads and nearby motels obviated the need for overnight accommodations and the need for space to meet the needs of expanded membership saw the last rooms eliminated in a 1968 renovation.

A full social program was in effect in the early days of the club, with informal dances every Wednesday and Saturday night.

Hagen, who broke the barriers of social ostracism against golf professionals, attested to the friendly atmosphere that prevailed when he said that the treatment he had received at Oakland Hills had spoiled him and made him accustomed to being treated as any golfer, pro or amateur, should be.

The barrier which Maple Road presented between the two courses was effectively overcome by installation of the world's largest arched aluminum pedestrian bridge.

Ben Hogan won with a total of 287 by shooting a final round 67 after which he was quoted as saying "I am glad I brought this course, this monster, to its knees."

There was some comment after the last round of the tournament of the effect that the tee markers had been moved so far forward that last day as to take some of the fairway traps out of play.

The Club once again hosted the U.S. Open in 1961 when Gene Littler's 281 nosed out Doug Sanders and Bob Goalby by a single stroke.

The next major tournament held at Oakland Hills was the 1964 Carling World Open which was won by Bobby Nichols whose 278 total beat out Arnold Palmer by a single stroke in an exciting finish.

During this Championship, the "Monster" yielded a little to sub-par rounds occasioned by soft greens, low rough and superb golf played by an extremely qualified field of top-flight golfers.

Chen blew a four stroke lead with a quadruple bogey on the fifth hole primarily by hitting his ball twice on one approach shot.

Despite a valiant effort on his part in a head-to-head duel with Andy North, the eventual winner, he was never able to recover from his disastrous experience on the fifth hole.

In 1976, both the downstairs and upstairs kitchens were completely remodeled and equipped to meet the demands of increased utilization by members of the Club's dining facilities.

Huge boulders, each 8–10 tons, containing commemorative plaques honoring twelve golfing greats, were installed along the first tee.

The grounds crew worked throughout the night draining water from many holes and reconstructed the damaged bunker in time for play on Thursday morning.

In January 1999, the club began a $16.25 million renovation project that included the Pro Shop, Bag Room, and remodeling and restoration of the clubhouse.

Frustrated with not being selected for any major championships for at least two decade period, Oakland Hills decided to undergo a complete renovation of the South Course from the fall of 2019 to July 2021.

The United States Golf Association, considering awarding Oakland Hills for their first U.S. Open since 1996, visited multiple times throughout the renovation.