The six-times world champion Davis was asked on Instagram by his old rival Hendry who would win if Trump and O’Sullivan locked cues with both men firing on all cylinders at the Crucible Theatre in Sheffield.
O'Sullivan is arguably the greatest player of all time, but many commentators believe 30-year-old Trump could be a future contender for that title. The retired duo of Davis and Hendry agree that peak O'Sullivan still has the edge.
"Ronnie’s best always wins,” said Davis, winner of the famous old pot in 1981, 1983, 1984, 1987, 1988 and 1989.
"Judd's game has got so strong mentally and his matchplay has improved, but you just have to favour Ronnie slightly if both are at their best," commented Scotsman Hendry, champion in 1990, 1992, 1993, 1994, 1995, 1996 and 1999.
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Trump lifted his first world title a year ago with arguably the greatest ever performance seen in a Crucible final firing seven centuries in an 18-9 demolition of the four-times world champion John Higgins.
O’Sullivan was fives times a winner at the celebrated Sheffield venue in 2001, 2004, 2008, 2012 and 2013.
In head-to-head meetings over 26 matches, the pair are locked at 13 wins each despite O’Sullivan turning professional in 1992, 13 years before his fellow Englishman Trump.
"Without trying to pander to the masses, I was involved like you (Hendry) in the process of the game getting better and better," said Davis, who retired in 2016 after a 38-year professional career. "To see players like Ronnie O'Sullivan and Judd Trump play the game..
"At one stage, I thought I was the best thing in the game and nobody was ever going to be better than me. To see those players, and what they do at the table, and the beauty with what they do, I can appreciate that now.
But if I was competing against them, I'd be hating it, but now I'm gasping with astonishment at some of the shots the modern day players play. Some of the shots Judd Trump plays are just astonishing. It's not just those two.
"For a while, at their best, the only player I thought who was capable of beating Ronnie was John Higgins because he had the game to beat Ronnie, but then you have the likes of Mark Selby and Neil Robertson who also come into the equation. It's a lot greyer an area now.
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"But Ronnie's best..it's tough to oppose him if you are thinking about them at their best. But then you (Hendry) at your best were great as well. It’s really tough to judge eras."
Davis admits O'Sullivan, who has made the most centuries in the history of the sport with 1038, has the added advantage of being able to perform well whether he is ahead or behind in a match.
Davis highlighted Hendry's 18-14 win over Jimmy White in the 1992 world final as an example of how to perform under extreme pressure. The Scotsman roared back from 14-8 down to win 10 straight frames in lifting the second of his seven Crucible titles.
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"I didn't have a great strike rate from behind," said Davis. "You came back against Jimmy White in the final, which was astonishing. I don't think I could have done that in a final, I don't know.
"But I see Ronnie O'Sullivan, he seems to not have a care in the world in his chair. He seems like he has the same game behind or in front. Then again, a lot more of the top players are capable of doing that."