Alex first began working with a Winterwood tutor in Year 4. Alex's introductory assessment identified that he was very able, but also a long way from the level required by the schools to which he was applying; City, Westminster and St Paul's.

Although Alex worked with Winterwood maths and reasoning tutors, his focus was English. Although raised in England for the majority of his life, Alex first learnt Russian and so found some aspects of English grammar and sentence construction difficult. Alex worked through a series of Winterwood resources and exercises to improve his grammar, with a particular focus on sentence construction and adding phrases and clauses to a sentence. In the end, Alex's English approved to such an extent that it was noted by his senior school as the stand-out entrance exam subject, and became his greatest strength.

Alex received firm offers from all three schools, and in fact was offered an academic scholarship by City of London School for Boys. Despite this, Alex chose to take up an offer from St Paul's. After a short-break, Alex began to work on common entrance subjects with his Winterwood tutors. As French proved troublesome, Alex worked with an inspirational Winterwood tutor who helped teach him the subject through French rap lyrics and music. Again, Alex improved hugely, and his common entrance grades were excellent. Alex went on to St Paul's, very well positioned to begin his senior school life.