Connelly's writing exhibits a self-deprecating humour and love of eccentricity that echoes the style of Bill Bryson. Similarly, he shares with several other writers a fascination with subject-matter that had not previously been a feature of traditional travel writing. Connelly began his career as a writer of books relating to sporting events, most commonly football. His breakthrough 2002 book, "Stamping Grounds", was his fifth, and followed the Liechtenstein national football team in their unsuccessful campaign to qualify for the 2002 FIFA World Cup. Connelly's 2004 follow-up, "Attention All Shipping", which was his first to deviate from football as its topic, has been listed as a best-seller and selected as "Book of the Week" by the UK radio station BBC Radio 4. "Attention All Shipping" (2004) was Connelly's first book not to take football as its central subject: again seeking out unusual destinations, he travels to each area mentioned in the shipping forecast made famous on BBC Radio 4.