Orange County Directory of 1899-1900 lists a Presbyterian Church, Reverend A.A. Parker, pastor.⁶¹ The Presbyterian Association would sell the sanctuary to St. Paul's in April 1907.⁵⁹

From at least this year until early 1923, the Watson general store is located at the northeastern corner of Hope and Railroad Street.⁶⁵

October 28: Investigation underway on the fire that nearly destroyed the wooden, Santa Fe depot in Olive which reportedly must be rebuilt.⁶⁵

May 9: Army aviator Lieutenant Joseph Dodge Park of New York is killed in a bi-plane crash in a barley field on the hill at Olive, the first aviation fatality in Orange County. [Sources: Roger Fitschen, Santa Ana Register, Jim Sleeper's Orange County Almanac of Historical Oddities (c) 1982, and FindAGrave.com.]

The Olive Road District map lists Libby J. Meats as the owner of the parcel of land across from Olive Grammar School, to the west of the railroad tracks.⁹ The 1913-14 business and resident directory lists the following businesses in Olive: Olive Public School, H.R. Wilson, principal; Olive Post Office, A.M. Lorenzen, postmaster; Olive Hotel, W.A. Campbell, proprietor.⁶²

Meyers Garage opens in a new brick building on the southwestern corner of present day Lincoln Avenue at Orange-Olive Road. (Source: Fred Meyers and Orange Public Library)

First National Bank of Olive organizes in spring, with business commencing in temporary headquarters on August 24.⁷¹ The bank moves on October 16 to the building erected by Henry C. Meyers on the northwestern corner of Hope at Railroad Street.⁷²

July: The residence and business directory lists the following information for Olive: Olive Garage, E.L. Cossairt, proprietor; Olive Heights Citrus Association, E.D. White, secretary; Olive Hillside Groves Packing House, J.D. Spennetta, secretary; Olive Hotel, W.A. Campbell, proprietor; Olive Ice Cream Parlor, M.H. Kelly; Olive Mercantile Co., general merchandise; Olive Milling Co., F.A. Blake, secretary; Olive Pool Room and Barber Shop, H.D.F. Heitshusen, proprietor; Olive Post Office, A.M. Lorenzen, postmaster.⁶³

April 12: Louis Schorn dies in Alhambra.¹⁸

H(arvey) Garber Brick Yards opens at the northwestern corner of Hope Street and Tustin Avenue.⁴¹

The City Directory lists Clement Lumber Co. (W.E. Clement) but does not include the business address.⁴⁸

April 27: Orange Post newspaper's "Greater Olive Expansion Edition" includes advertisements from the following businesses in the Olive district: Olive Realty Company (Meyers Building, opposite First National Bank, H.L. Stinchfield, Manager), Olive Service Station (Riverside and Olive Blvds., Chas H. Squires), First National Bank of Olive (organized in 1916), Peppers Fruit Co. (night phone W.J. Kadau, V.H. Fross), Central Milling Company (JNO. M. Gardiner, President, John W. Ahoff, Vice President, A.B. Walbridge, Secretary), H. Garber Brick Yards (Santiago Blvd., Harvey Garber), Olive Cigar Store / Billiard Parlor / Barber Shop (A.J. Lee & Son), Olive Heights Citrus Association, Olive Cash Market (Anaheim Blvd., opposite First National Bank, Theo H. Mieger, Properietor), Olive Mercantile Co. (Anaheim Blvd., opposite First National Bank, J. Hecke, Proprietor), The Olive Store (D.E. Trefry & L.O. Holman, Proprietors), Olive Restaurant and Confectionery (J. O'Grady & Harry Sullivan), Olive Garage (Olive Blvd., C.F. Bliss, Proprietor), Olive Hillside Groves, Inc. (W.A. Greenleaf, President, C.O. Heim, Vice President, F.B. Maxwell, Secretary and Manager, Directors W.A. Greenleaf, C.O. Heim, J.B. Bush, August Lemke and R.H. Paulus). (Source: Phil Brigandi)

June: A single-story brick structure is completed at the northeastern corner of Canyon Way (Railroad Street) and Hope. This building houses the U.S. Post Office, Olive Mercantile Company general store, Olive Cafe restaurant, Olive Pharmacy and drugstore, and Olive Bakery.⁵⁹

Peppers Fruit Company is renamed Olive Fruit Company. (Source: Tom Pulley) In March 1926, the Company would add a second packing house at 805 E. Center in Anaheim.⁴¹

The Orange County Directory lists the following information for Olive: Clement Lumber Co. (W.E. Clement) T.A. Bennett, manager, Canyon Way—which would become the present-day Orange-Olive Road; Olive Bakery (F.S. Beecher) Hope St.; Olive Cafe (Mrs. Ella Colgrove) Canyon Way; Olive Fruit Co., W.J. Kadan, manager, P.O. Box 187; Olive Garage (E.P. Ehlen); Olive Hardware Co. (Schlueter Bros.) Canyon Way; Olive Heights Citrus Assn., Ben H. Cole, secretary-manager, Canyon Way; Olive Heights Sanitarium (Mrs. A.G. Heitshusen) Palm Avenue; Olive Hillside Groves, Inc., F.B. Maxwell, manager, Canyon Way; Olive Mercantile Co., D.C. Feemster, manager; Olive Pharmacy (G.B. Stewart) Canyon Way corner Hope; Olive Post Office, L.G. Holman, postmaster, Canyon Way; Olive Realty Co. (H.L. Stinchfield) Anaheim Road; Olive Realty Exchange (Adolf Ehman, A.A. Ehman, A.R. Robbins) Canyon Way; Olive Store (L.G. Holman) grocers and post office, Canyon Way; Standard Oil Co., Anaheim Road corner Canyon Way.⁴¹

July 22: Central Milling Company is put up for sale.⁶⁵ Soon after, Harvey Garber begins operating Padre Tile Company out of the buildings on this site. (Source: Phil Brigandi)

The Olive Improvement Association—in coop with the city of Placentia—subsidizes the Olive Chronicle newspaper, which runs for six months.⁴⁴

The Orange County Directory lists the following information for Olive: Clement Lumber Company (W.E. Clement, owner, T.A. Bennett, manager, Canyon Way), Olive Bakery (listed at Hope and Canyon Way in the 1929 Directory, and at Santiago Boulevard in its last entry in the 1934 Directory), Olive Cafe (listed at 3 Canyon Way in the 1927 Directory—its last entry at this address would appear in the 1934 Directory), Olive Cash Market (Theo H. Mieger—this is its first and last entry in the annual Directory), Olive Fruit Company (A.J. Miller, manager—the 1927 Directory lists the branch location on Main Street at the corner of Olive Avenue and the main office in Anaheim), Olive Garage (E.P. Ehlen), Olive Hardware Company (W.C. Schlueter, Canyon Way—this is its last entry in the annual Directory), Olive Heights Citrus Association (Ben H. Cole, manager), Olive Hillside Groves, Incorporated (F.B. Maxwell, manager), Olive Mercantile Company (D.C. Feemster, manager, grocers—listed at Anaheim-Olive Boulevard in the 1927 Directory and at 5 Canyon Way in its last entry, the 1933 Directory), Olive Pharmacy (G.B. Stewart, Canyon Way, at the corner of Hope), Olive Post Office (L.G. [Leonard George] Holman, postmaster), Olive Store (L.G. Holman, grocer).⁴¹

Harvey Garber loses H. Garber Brick Yards to Attorney Arthur E. Koepsel. The name of the business is subsequently changed to Mission Clay Products Company. Garber also loses Padre Tile Company to Koepsel.⁴⁴ Proprietors are listed as Koepsel and Sidney Aronson.²⁵

February 10: Russ Heman is born Russell Frederick Heman in Olive. Son of softball pitcher Rudy August Heman, Russ would be signed by the Chicago White Sox as an amateur free agent in 1952. Heman would debut as a major league pitcher with the Cleveland Indians on April 20, 1961, and would later pitch for the California Angels (known today as the Los Angeles Angels of Anaheim). His final game would be on June 18, 1961.²⁷

The First National Bank of Olive closes due to the "Stock Market Crash of 1929." In later years, Henry C. Meyers' family would reside upstairs in this building.⁹

The Orange County Directory lists the first entry for Olive Service Station (Canyon Way—its last entry would be in the 1939 Directory).⁴¹

Fire Station #20 (Olive Volunteer Fire Dept.)—the new adobe firehouse—is constructed of adobe bricks on Orange-Olive Road, near the northwestern corner of Anaheim-Olive Boulevard.³⁰ Prior to this time—according to Margaret Hughes' hand drawn map dated in the 1940s—there is a library to the south of the auditorium at the Civic Center, and a bus garage at the northwestern corner of Buena Vista and Orange Avenue. On the southeastern side of Santiago (Lincoln Avenue) at Orange-Olive Road, the map shows a cafe, a blacksmith shop (likely Grant Hughe's welding shop listed in the 1948-49 Jay Gee Business Directory), and a pool hall—the same structures included in the 1929 Sanborn map. To the immediate west of the Olive Garage—at the southwestern corner of Anaheim-Olive and Orange-Olive Road—is a grocery store, perhaps the same one at 6 Anaheim-Olive Boulevard on the 1929 Sanborn map.⁹

The 1948-49 Jay Gee Business Directory for Orange, Olive, El Modena and Villa Park lists the following businesses in Olive: Olive Beauty Salon (corner Main and Ocean View, Orange, 581-J), Nichols Cafe, Huge's Grant [Grant Hughes] Welding Shop (P.O. Box 23).