These files are a mix of events from different points in Barney Oldfield's career.

Oldfield vs. Chevrolet: Lima Driving Park

These articles are from 1909. The writer specifically mentions Louis Chevrolet's Cobe Trophy road race victory in Crown Point, Indiana, which took place in 1909. This event took place on a half-mile track, and reports Barney Oldfield's track record setting run.
Oldfield vs. Christie

This package of articles is from 1909, and, perhaps, 1908. One article touts the prowess of J. Walter Christie's front wheel drive monster - clearly from 1909 as it mentions Joe Matson's 1909 Indiana Trophy. Another article discusses two deaths on California dirt tracks and how it must spell the doom of track racing. A third article describes how Oldfield got "punked" by a group of good old boys who took him before a judge to assess a $200 speeding fine - and then surprised him with a special luncheon.
Oldfield Retires - Again

This collection is a hodgepodge of clips demonstrating the lack of organization and sourcing in the Barney Oldfield scrapbook. Perhaps the most interesting artilce is one that announces one of Barney Oldfield's many retirements from auto racing. Throughout he suggests that he has simply lost interest. My best guess is that this article is from 1907 because it references his stint in Vaudeville and Broadway, which was late 1905 and early 1906. Oldfield's career is most poorly documented in the 1906-1907 time frame and I believe this is due to two factors.
Oldfield, Christie, Strang Barnstorm

I am almost certain this collection of articles is from the autumn of 1907. Lewis Putnam Strang raced for his uncle, John Walter Christie, after the latter broke his wrist in September 1907. He then began driving an Isotta for a very successful year of road racing in 1908. That means the article in the far left column of the first page of this collection is almost certainly October 1907. Also, the article immediately beside it references the Strang article. Wherever the men were, they were putting on speed exhibitions in the Fall of 1907.
Oldfield in Stearns for 1908

This is another messy collection of clips from Barney Oldfield's scrapbook. Mingled together are articles from 1908, 1903 and 1904.
Oldfield, Christie, De Palma Barnstorm

The primary article in this collection reports on a 1908 Minneapolis-St. Paul track race. This covers the results of a contest which is described in another article on firstsuperspeedway. The featured drivers were Barney Oldfield, Walter Christie and a young upstart by the name of Ralph De Palma. In 1908 the popular notion was that stock car racing was the only meaningful speed contest as it provided more meaningful insight to the speed and durability the public could actually purchase.
Oldfield, "Senator" William Morgan, 1909-10

This collection of articles is from 1910 & 1909. On the first page, far left column is an article written by "Senator" William J. Morgan, the man who conceived the original Ormond-Daytona Beach time trials from 1903 through 1910. Morgan's article promotes another proposed attraction that would pit four marketable drivers in a contest that he obviously believed could be billed as a major championship.
Oldfield's Antics & Driving Whipple's Stearns

In yet another example of the general messiness of the Barney Oldfield scrapbook, this collection mingles articles from 1904 and 1908. The first article on the left of the first page is about what the unnamed newspaper claims is the first auto race in San Diego. Who knows if it is true, but because it mentions Oldfield on the Winton Motor Carriage Company Bullet No.3. Another article is the most amusing in that it describes Oldfield getting into a fight with some "liquored-up drunks" who were riding in a wagon pulled by a horse.

A file of research on Louis Chevrolet, the leader of the Chevrolet brothers, which included Arthur and Gaston, who won the 1920 Indianapolis 500. Chevrolet was an excellent driver, mechanic and engineer. He struggled with his business dealings, losing his interest in the Chevrolet Motor Company, which eventually became part of GM. Several other efforts went south as well and he was reduced to humble means by the time of his death in 1941.

Chevrolet Wins Atlanta 200 - 1909

This hodgepodge of clips comes from Barney Oldfield's personal scrapbook, but the feature content has little to do with him. The main article is about a race that took place in the autumn of 1909 at a two mile road course near Atlanta. Louis Chevrolet won that race handily, his only setback being an oil fire under the hood of his Buick, which he quickly extinguished. There is another article covering the events of the Indianapolis Motor Speedway's little known speed trial in December 1909. This event was to test (and promote) the newly paved track that was quickly nicknamed the Brickyard.

This category for the 1908 Briarcliff Road Race currently includes four files sourced from Barney Oldfield’s scrapbook and a few from local Indianapolis newspapers. The race was won by Lewis Strang in an Italian Isotta. The field was large for the day – 22 competitors in all, including: Ralph De Palma, George Robertson, Herb Lytle, Barney Oldfield and Emanuel Cedrino. Briarcliff proved to be the final road race for the Italian ace Cedrino, who was killed in his Fiat at Pimlico the following month.

Briarcliff - Herb Lytle's POV

This article provides driver Herb Lytle's perspective on the Briarcliff road race. He was extremely critical of the course which provides insight to why the race was never conducted again. Some of his descriptions are colorful and provide a sense of the setting on race day. The course was crowded with spectators who apparently became unruly around the cars.