May 1
Former three-time Formula One world champion, Ayrton Senna, considered by many to be the world's best F1 driver, died at the San Marino Grand Prix in Imola, Italy, after his car slammed into a concrete wall at high speed. (1994) 

Stirling Moss drives a race car for the first time in over a year, since a crash that nearly killed him, in a test session at Goodwood, England. His driving is not up to his own standard, and he retires from competition (1963).

May 2
NASCAR Sprint Cup Series driver Kyle Busch, is born in Las Vegas, Nevada,  USA. (1985)

Chris Bye, race driver and author of Crash Test : My Brother's Accident and the Race of Our Lives. A true-life story of his brother Rick's nearly fatal highway accident in North Carolina and epic struggle to recover from severe brain damage. Born on this day in St. Catharines, Ont. (1960)

May 3
Nelson Piquet of Brazil wins the "Grand Prix of San Marino" at Autodromo Enzo & Dino Ferrari, Imola, San Marino. Canada's Gilles Villeneuve was 7th in a Ferrari. (1981)

May 4
Hurley Haywood, five-time winner of the "Rolex 24 at Daytona", and three-time "24 Hours of Le Mans" winner, born in Chicago, Illinois, USA. (1948)

The late Peter Gregg, a four-time winner of the "24 Hours of Daytona", and owner of Brumos, a Jacksonville, Florida car dealership, born on this day in New York City, New York, USA. (1940)

May 5
Boris "Bob" Said, the first American to win a road race in Europe after World War II, and father to NASCAR road course ringer Boris Said 111, was born on this day in New York City. (1932)

Klaus Ludwig, 3 time "24 hour of Lemans" winner, born in Bonn, Germany. (1949)

Daryl Harr, NASCAR Nationwide Series driver, born in St. Albert, Alberta, Canada. (1982)

May 6
51-year-old Harry Gant, racks up his 12th NASCAR Winston Cup career victory, in the "Winston 500" in Talladega, Alabama. In doing so, Gant bettered his own record as the oldest man ever to win a NASCAR event. (1991)

Paul Tracy of Toronto drove his team Kool/Green, Reynard / Honda to a third place finish at the CART "Lehigh Valley Grand Prix" at Nazareth Speedway, Nazareth, PA. (2001)

May 7
Patrick DePailler of France wins the "Grand Prix of Monaco" at Circuit de Monaco, Monte Carlo, Monaco. It was his first Formula One victory. Canada's Gilles Villeneuve finished 12th after a crash on lap 62. (1978)

May 8
Canadian racing legend and Hall of Fame member Gilles Villeneuve, was killed during practice for the Belgian Grand Prix at Zolder. (1982).

Bobby Labonte, the 2000 NASCAR Winston Cup Series champion, born in Corpus Christi, Texas, USA. (1964)

May 9
Louis Schwitzer, winner of the inaugural race at the Indianapolis Motor Speedway died on this day. In front of some 12,000 spectators, Schwitzer, an automotive engineer, won the two-lap, five-mile inaugural race at the Indianapolis Motor Speedway, with average speed of 57.4 mph. In 1965, Schwitzer suffered a stroke while riding a horse on his farm. He was paralyzed, and for a time lost his ability to speak English, reverting to Hungarian where he died, on this day in 1967.
For more see; Louis Schwitzer wins first race at Indianapolis Motor Speedway

J.R. Fitzpatrick, NASCAR Canadian Tire Series and Camping World Truck Series driver, born in Cambridge, Ontario, Canada. (1988)

May 10
Automotive icon, builder, racer, and entrepreneur Carroll Shelby, dies in Dallas, Texas, USA, at the age of 89. (2012)

Helio Castroneves, three time winner of the Indianapolis 500, born in São Paulo, Brazil (1975)

Arie Luyendyk, also known as "The Flying Dutchman", set a single lap, track record in practice for the Indianapolis 500 with an average speed of 239.260 mph (385.052 km/h). (1996)

May 11
Paul Tracy of Toronto finished 1.805 seconds ahead of Maple Ridge, BC native Greg Moore for an all Canadian 1-2 finish at the CART "Hollywood Rio 400K" at Autodromo Nelson Piquet, Rio de Janeiro, Brazil. (1997)

May 12
19-year-old Adam Petty, son of Winston Cup driver Kyle Petty and grandson of NASCAR icon Richard Petty, is killed after crashing into a wall during practice for a Grand National race at Loudon, New Hampshire. (2000)

Melvin "Tony" Bettenhausen, killed in a crash at Indianapolis while testing a Stearly Motor Freight Special vehicle for Paul Russo. (1961) 
Bettenhausen was the father of Gary Bettenhausen, Tony Bettenhausen, Jr. and Merle Bettenhausen. He was inducted in the National Midget Auto Racing Hall of Fame in 1985, the International Motorsports Hall of Fame in 1991, and the Motorsports Hall of Fame of America in 1997. 

May 13
Jody Scheckter driving a Ferrari, wins the "Grand Prix of Belgium" at Circuit Zolder, Heusden-Zolder, Belgium. Scheckter's teammate, Gilles Villeneuve of Canada was 7th. (1979)

May 14
Stirling Moss wins the Monaco Grand Prix in a Lotus 18-Climax entered by Rob Walker. Moss' second straight Monaco win (1961).

May 15
Al Holbert and Jim Trueman drive a March-Porsche to victory in the IMSA Camel GT race at Charlotte, North Carolina, USA (1983).

May 16
Dick Trickle, 1989 NASCAR Winston Cup Series "Rookie of the Year" and billed as the winningest short track driver in history, died from an apparent self-inflicted gunshot wound, in Boger City, North Carolina, USA. (2013)

Horst Kroll of Toronto, 1986 Can -Am Champion and Canadian Motorsport Hall of Famer, born in Germany. (1936)w

May 17
Scott Brayton, killed in practice after qualifying for the pole position for the "Indianapolis 500". (1996)    

May 18
Team Lotus, one of the most successful teams in history, makes its Formula One debut in the Monaco Grand Prix. (1958)

Hiro Matsushita becomes the first Japanese driver to qualify for the "Indianapolis 500". He qualifies 24th. (1991)

May 19
Jack Brabham, 3-time Formula One champion, the Brabham racing team, and race car constructor that bore his name, died in Gold Coast, Queensland, Australia. (2014)

Bill Holland, 1949 "Indianapolis 500" winner, died of Alzheimer's disease in Tuscon, Arizona, USA. (1984)

Dario Franchitti, a four-time IndyCar Series Champion and three-time "Indianapolis 500" winner, born in Scotland. (1973)

May 20
Tony Stewart, three time NASCAR Sprint Cup Series Champion and team owner, born in Columbus, Ohio, USA. (1971)

May 21
Everett "Cotton" Owens, NASCAR racer and team owner, born in Union, South Carolina, USA (1924).

May 22
Paul Newman, legendary actor, philanthropist and automobile enthusiast makes his onscreen racing debut in the action-drama film "Winning."  (1969)

Luigi Fagioli, drives a Mercedes-Benz W25 to victory in the Monaco Grand Prix. He became the first driver to lead at Monaco from flag to flag. (1935)

May 23
Bryan Herta, former Indycar driver and team owner, born in Warren, Michigan, USA (1970)

Former F1 and Indycar driver Rubens Barrichello, born in São Paulo, Brazil. (1972)

May 24
Chip Ganassi,currently the owner and CEO of Chip Ganassi Racing which operates teams on the IndyCar Series, NASCAR Sprint Cup Series, and Tudor United SportsCar Championship, born in Pittsburgh, Pennsylvania, USA. (1958)

May 25th
The late Jim Trueman, driver, owner of  Mid-Ohio Sports Car Course and the Truesports racing team is born. (1935)  

Canadian Motorsport Hall of Fame member Bill Adam is born on this day in Airdrie, North Lanarkshire, Scotland. (1946)

International Motorsports Hall of Fame member Henry "Smokey" Yunick was born on this day. (1923)

May 26th
Sam Posey, retired American racing driver and sports broadcast journalist is born in New York City, New York, USA. (1944)

On the 199th lap, of the the 86th Indianapolis 500, second place Paul Tracy of Toronto attempted to pass Hélio Castroneves for the lead in the third turn. At the same time, a crash occurred on another part of the track, bringing out the caution flag. Indy Racing League officials ruled that the yellow came out before Tracy completed the pass, and Castroneves was declared the victor. After an official protest was filed, and after an appeals hearing, Castroneves' victory was upheld. (2002)

May 27th
Canadian Motorsport Hall of Fame member Scott Goodyear of Toronto, finished 2nd at the 81st Indianapolis 500 behind teammate and polesitter Arie Luyendyk. With two laps to go, Luyendyk led Goodyear. A caution came out on the 199th lap, but the pace car did not come out to pick up the field. Without warning, the green and white flag were displayed at the starter's stand on the final lap, signifying the field was back to racing conditions. None of the cars in the field were prepared for the restart, and yellow lights remained illuminated for many seconds afterwards. Luyendyk held on to win, but controversy erupted regarding the officials' poor handling of the situation. Less than a month later, USAC was permanently removed from sanctioning the IRL and Indy 500, in favor of in-house officiating. It was the third time in his career that Goodyear narrowly lost the Indy 500 in the closing stages.

May 28th
The 79th Indianapolis 500 is won by Jacques Villeneuve. On lap 190, with the field coming back to green on a restart, leader Scott Goodyear of Toronto passed the pace car in turn four, and was assessed a stop-and-go penalty. Goodyear refused to serve the penalty, claiming that the green light was on, and stayed out on the track. Officials stopped scoring him on lap 195, which handed fellow Canadian Jacques Villeneuve the lead of the race, and ultimately, a controversial victory. (1995)

Eppie Wietzes of Toronto, a two-time Canadian Driving Champion and Canadian Motorsport Hall of Fame member is born. (1938)

May 29th
Four time Indy 500 winner Al Unser Sr is born on this day in Albuquerque, New Mexico, USA. (1939)

Stirling Moss wins the Monaco Grand Prix in a Climax-powered Rob Walker Lotus 18. It was the first Grand Prix win for Lotus. (1960)

May 30th
Mario Andretti led 116 laps and won the 53rd Indy 500 for car owner Andy Granatelli. The car in which Andretti won the 500 is on display at the Smithsonian, while a replica made from the original blueprints sits on display at the Indianapolis Motor Speedway Hall of Fame and Museum. (1969) 

Ray Harroun drives his single-seater Marmon Wasp to victory in the inaugural Indianapolis 500. (1911)

Clint Bowyer, NASCAR Sprint Cup driver and 2008 NASCAR Nationwide Series Champion, born in Emporia, Kansas, USA. (1979)

May 31
The 49th Indy 500 was won by Jim Clark, winner of two F1 World Championships, in 1963 and 1965. Mario Andretti, who ran no lower than 6th all afternoon, came home third, and won the Rookie of the Year. Billy Foster of Vancouver became the first Canadian to ever race in the Indianapolis 500, finishing 17th after a mechanical problem forced him out on lap 85. Foster was inducted into the Canadian Motorsport Hall of Fame in 1993. (1965)

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