The mild-mannered coach had a hot argument with the man, said to be a Pakistan-based bookie who was at the world cup with Dawood's brother Anees Ibrahim, according to a report in The Sun.
Jamaican government officials said two Pakistan players had told police of the row between the coach and the bookie.
The two players were said to have spoken of a furious bust-up in their statements to cops.
''Bob Woolmer said he had thrown a bookie out of his room. He didn't give a reason,'' an official was quoted as saying by the tabloid.
Deputy Commissioner of Police Mark Shields, who is leading the inquiry, refused to confirm the incident, but said police would be investigating it.
''This issue has come up before but we have so far been unable to substantiate it,'' Shields said.
''But we are prepared to consider it further now we have names and more details. We will be investigating,'' he added.
Meanwhile, Shields refused to give clean chit to Pakistan players in the Bob Woolmer murder case and described team spokesman Pevez Mir's comment as 'pretty inaccurate' that Inzamam-ul Haq and Co were not suspects anymore.
''That is a pretty inaccurate statement because nobody at this stage could be ruled out of the inquiry,'' Shields told BBC Radio Five Live.