Question: Who has won the most tennis matches in history?
Disambiguated questions and answers: question: Who has won the most tennis matches in history as male?
Who has won the most tennis matches in history as female?
answer: Jimmy Connors
James Scott Connors
Serena Williams
Serena Jameka Williams
Natural Questions answer: 1256 (from the Wikipedia article "List of Open Era men's singles tennis players by career match wins")