So this "joke" doesn't work for many reasons, first would be that there hasn't been a single X/2 on Middlesbrough Vs Millwall in past 35+ years, in order for a "joke" to make sense the set up needs to be an actual quote, fact, news etc, preferably a recent one, all of which you don't have...
Second, Fagioli is famously bad at gambling, hence the big debt he recorded, if it was the other way around he wouldn't have reported himself for being awesome at gambling and winning millions and millions from it, so the punchline of the "joke" should be Fagioli giving Motta an obvious bad advice to bet a ton of money on..
For example, "how I heard, Motta is upset because Fagioli told him to bet a ton of money on the Beatles winning a Grammy for "Best new artist" the other night"..
Which is an okay "joke" as it portraits both of them like dumb incompetent guys, also the set up is okay because the Beatles were in fact nominated for "Record of the year" with their "Now and then" project, but the award went to Kendrick Lamar in the end...