1920: (Winner: Gaston Chevrolet)

One of the Indy 500 ‘traditions’ that remains to this day started in 1920 with the four-lap qualifying system introduced. A “Chevrolet” appears in victory lane for the first time – but not what I first thought: Gaston Chevrolet, driving a Monroe-Frontenac built by brother Louis took the first win for ‘a’ Chevrolet!  

Winner Gaston Chevrolet

1921: (Winner: Tommy Milton)

Tommy Milton won the first of his two Indy 500s. The race was again dominated by Ralph dePalma. He had a two-lap lead when a connecting rod broke on lap 112. DePalma retired with one win and 612 laps led – a record that would stand until tied by Al Unser Sr in 1987. Man, the luck Ralph had there – clearly very fast and an awesome racecar driver!

Louis Fontaine crash

1922: (Winner: Jimmy Murphy)

Jimmy Murphy led a Duesenberg blitz (eight of the top 10) and became the first driver to win from the pole. He ran a new 183-cubic-inch, DOHC 32-valve straight-eight engine designed by Harry Miller. Miller engines and cars would win nine of  the next 12 races. Duesenberg some years later was the favored car brand of enigmatic billionaire, Howard Hughes.

Winner Jimmy Murphy

1923: (Winner: Tommy Milton)

Indiana Governor Warren McCray vetoes a bill to outlaw “commercial sports” on Memorial Day and saves the event. I like this guy! From here on in, the Indianapolis 500 would be held on Memorial Day Weekend – another tradition that continues to this day. Ridealong mechanics are no longer required and Tommy Milton becomes the first repeat winner. 1919 winner, Howdy Wilcox relieved Milton from laps 103-151 so his hands could be bandaged for blisters. On lap 22, Tom Alley crashed on the backstretch. This crash killed a 16-year-old spectator, Bert Shoup.

Tommy Milton got his second win in '23

1924: (Winner: L.L Corum & Joe Boyer)

A.W. Kaney, of Chicago’s WGN radio, put the 500 on the airwaves with live reports for the first time. L.L. Corum started the race in the #15 and was replaced by Joe Boyer who went on to win in the first supercharged Duesenberg. The pair were classed as “co-winners”.

First co-winners

1925: (Winner: Pete DePaolo)

Pete DePaolo became the first driver to average more than 100 mph (160kph) for 500 miles (800km), winning at 101.1 mph (161.76kph) in a supercharged Duesenberg.

Pete DePaolo averaged more than 100mph

1926: (Winner: Frank Lockhart)

Duesenberg’s success with boosted engines has not gone unnoticed. With a new, 91.5-cubic-inch formula, every car in the field of 28 is supercharged. Harry Miller’s cars swept the top four spots, led by rookie Frank Lockhart who was in front when officials called the race after 400 miles (640km) because of rain.

Frank Lockhart won a rain shortened 400 mile race

1927: (Winner: George Souders)

George Souders becomes the first driver to win the race unaided by a relief driver or ride-along mechanic and he does it by an incredible eight laps! On August 15, Eddie Rickenbacker buys the Speedway for $US700,000 with the help of a group of Detroit investors. Rickenbacker – now Indianapolis Motor Speedway President –  has his own history at the Speedway, having started the Indy 500 four times – he was also a WWI Fighter Pilot!

George Souders won unaided by eight laps

1928: (Winner: Louis Meyer)

Rookie Louis Meyer would win the first of his three Indy 500s after being a relief driver the previous year. He started 13th and led 19 of 200 laps to win $28,250 in prize money.

Louis Meyer won his first of three 500s

1929: (Winner: Ray Keech)

This year saw a real unique first when Maude A. Yagle became the first female owner to win the Indianapolis 500. She would be the first of many amazing stories of women at the 500 over the years. Ray Keech was Ms. Yagle’s driver that took the checkered flag. Tragically, Keech was killed at Altoona Speedway two weeks later. Another feature that remains today at the Speedway was the expansion to include a golf course with nine holes on both the inside and outside of the track.

Ray Keech died two was after his '29 victory