[2] Alleyne was noticed as a cricketer as a teenager while attending the Holy Cross College in Ryde, playing for the Catholic Young Men junior cricket team which competed for the Martin Shield.

[8][9] In October 1927 a report noted Alleyne was showing very promising form and had an ideal temperament suggesting that "bigger things must be expected of him in the near future.

"[10] In November a report described him as a "fine batsman" and praised his play on the leg side and noted that while he had a weakness to balls on his legs he had still played some "excellent shots" to yorkers,[11] and another report called for him to be selected for the New South Wales Second XI.

[12] In December he was selected in the New South Wales First-class side for a match against Tasmania.

He scored one run and a duck in his innings, and a report noted that he seemed to have been affected by the fact it was his debut and suggested that he may have more confidence if selected again, however it was his only First-class game.