May 27th

    May 27th, 1951

Fergus Anderson wins the 500cc class Swiss Grand Prix at Circuit Bremgarten in Bern, Switzerland on a works Moto Guzzi.

Anderson took the 1953 350cc World Championship for Guzzi, and again in 1954. He died on May 6, 1956 after an accident on a "Dustbin" BMW at the Floreffe in Belgium.
Fergus Anderson

    May 27th, 1990

Kevin Schwantz and Wayne Rainey finish 1-2 at the 1990 German Grand Prix at Nurburgring.
Schwantz and Rainey finish 1-2

    May 27th, 1965

Antonio Ligabue.
In 1961 his first solo exhibition was held at the La Barcaccia gallery in Rome. He had an accident on one of his 16 Moto Guzzis and the following year he was stricken with paralysis. Ligabue died in Gualtieri on 27 May 1965.
A compelling film of his life was produced in 2020, "Volevo Nascondermi" ("Hidden Away"), and another in 1978, "Ligabue".
en.wikipedia.org/wiki/Antonio_Ligabue