The easiest route to this is to manage a dominant team in a weaker league. I unlocked this while using Welsh club TNS as part of the Unrest At Home challenge.
TNS starts the scenario at the top of the table, and I was able to stay there by going for instant results with the “go for the big win” plan. The Welsh season is fairly short in the scenario (you take over halfway through the season) and the league only has 10 teams, making it easy to get multiple players on the team of the year list at the end of the season.