Maria Teresa de Filippis in the 1953-model Maserati 250F s/n 2501 (later 2523) at Italian Grand Prix at Monza (Italia) on 9 September 1958.  Probably before the race (practice runs)?  She had bought the car earlier that year<a rel="nofollow" class="external autonumber" href="http://www.barchetta.cc/english/All.Maserati/Detail/2501.250F.htm">[1]</a>, but did not finish the race.<a class="external autonumber" href="https://en.wikipedia.org/wiki/1958_Italian_Grand_Prix">[2]</a>
Alan R. Smith (ca.1904–2008)
<a rel="nofollow" class="external autonumber" href="https://i.pinimg.com/originals/10/bd/90/10bd902a7e7f8212f6f79544955c7c6f.jpg">[3]</a>