So I'm at my last club in mine and a friends pentagon challenge.
Super far ahead when it comes to the continental trophies. (4-2)
My path:
5 seasons at Nanjing then won the cup
2 seasons at Supersport in South Africa before winning the cup
2 seasons at Tigres before winning
2 seasons at Palmeiras before winning
Took me a season to find a job. Was really wanting United but their manager (Marcelinho), kept hanging on by a thread. Didn't want another Prem side, even though Arsenal and Newcastle became available. Other clubs I could have got but didn't want to manager were AC Milan, Roma and Juve. Finally took over Leipzig about half way through their seasons. 4 games left to try and earn a CL spot this year, but I think unlikely.
Friends path:
Sacked at Gungzao (impossible job to be fair
)
Won the league with Halifax wonderers
Left for Gil vicente (At the time I could not believe he got such a good job for the standard, spent two seasons with them.
Got offered a job in the Eredevisie, but decided to go to South Africa
Won their cup in his second season (same year I won in Asia)
He crossed over to Urawa red dragons and won their cup in two years (At this point we're level in the challenge)
When I went to Mexico, he decided MLS was the best option as all the clubs were rich. This is where it all went down hill. (transfer rules etc made it an impossible task)
In the second season, I beat him in the continental cup quarters, and he quickly realised America wasn't gonna happen.
Made the shock move to Brighton, had a decent season then moved to Spurs.
He's currently in his second season right now, in the semi's of the Champions league and probably going to win it at this point. Had some huge luck in the knockouts so far, but finding form at the right time.