In his 26 years as Holy Father, Pope John Paul II met with His Holiness the Dalai Lama more than he met with any other dignitary. Wikipedia says they met eight times.
Several published accounts said the Vatican purposely kept meetings between the Pope and HH the Dalai Lama “low-key” in order to keep from upsetting China.
“I do not want to create any embarrassment, any inconvenience,” His Holiness said during a 2003 visit with the Pope. “My main sort of interest, or main purpose or goal is promotion of human values and promotion of religious harmony.”