Cyril Trailer's appearances for Wales Schoolboys in 1932-33 impresed Tottenham, as he scored three times in two games.
Initially, Cyril joined the Junior team and worked in Hayward's in Enfield, lodging in Ponders End at the time.
Another impressive scoring showing, grabbing two goals in a 7-1 win over South Wales Juniors at the Lane, earned Trailor an amateur contract with the club the very next week.
At the tender age of 16, the centre forward made his reserve team debut and signed as a professional for Tottenham's nursery team Northfleet United and his haul of 46 goals in the 1937-38 season won him a Kent Senior Cup winners medal.
In the October of 1938, Cyril signed as a professional with Tottenham and his first game in the first team came in December 1941, as Spurs faced Aldershot in a war-time match, by which time he had converted to a half back.
During World War II, Trailor served with the Royal Artillery and in 1946, he returned to the club and played for the first team and A team. In total, Cyril made 11 League matches and one FA Cup match, without a goal and below the first team, he scored 24 goals in 118 games.
In July 1948, Trailor joined Leyton Orient for a fee of £600 and he made 40 first team matches before joining Bedford Town. Cyril retired from the game when an ankle injury prevented him playing any further, so he returned to his home town and was said to work for the Hoover company there.
Cyril died on 28th August 1986 in Merthyr Tydfil.