Nyorai kupfuurira kweiyi ndima - Gilmour akabatana neLovat Scouts muna 1937 uko akawana basa rake. Akazobatana neSeaforth Highlanders muna 1939. Pakati pa1942 na1943, aive ne2nd Seaforth mu51st Highland Division ye8th Army muNorth Africa mushandirapamwe. Akapihwa Military Cross paHondo yechipiri yeEl Alamein, aine Bar kuMC yekuratidzira kumwe kushinga pamberi peGerman Afrika Korps paHondo yeWadi Akarit
. Akatora rutivi mukurwiswa kweSicily. Akadzokera kuUnited Kingdom muna 1943. Kubva muna 1944, akashanda muNormandy, Netherlands, uye kuGermany kwaakagamuchira Distinguished Service Cross kubva kuUnited States.