I don’t think you could have teams or even single individuals traveling internationally fast enough for leagues to have games often enough until you have trains or steamships. Two or three events per year isn’t going to be enough. I don’t think you could develop the technological advancements...
For starters, most of the recipes you mention depend upon ingredients from Asia, the new world, the tropics and perhaps Africa. I’m not sure how you’d get them to the Roman Empire at all, let alone fast enough to not have them spoil.
As I remember it, Loreena McKennit lost her fiance in a boating accident just about when she was starting to have success with songs like Mummer's Dance. She was so devastated that she mostly withdrew from music for 6-7 years. She didn't release any recordings from 1998-2005 and didn't perform...
I just have a small quibble here. Tom Hanks was 9 years old in 1965 and probably isn't the best source on what was happening then, especially about Jim Morrison, who was attending UCLA while Tom Hanks was in Northern California.
Great timeline! I'm enjoying it very much.