Conversation so far:
When did Steve Waugh have issues in the Caribbean?
Mark Taylor retired at the end of the 1998–99 season and Waugh replaced him as Test captain, beginning with a tour of the Caribbean.
What team did Steve Waugh play for?
As Australian captain from 1997 to 2004, he led Australia to fifteen of their record sixteen consecutive Test wins, and to victory in the 1999 Cricket World Cup.
How did the Kiwi's play first with Steve Waugh?

Question: How did Waugh struggle?
Self-contained rewrite: How did Steve Waugh struggle?