4. Nani
It is safe to say that Nani never fulfilled his great potential despite showing flashes of his genius on many occasions. Perhaps it was not his fault rather a comparison with another Portuguese winger who followed a similar path from Sporting CP to Manchester United and set the bar too high to reach.
Signed at the age of 16, Nani had to spend just two years in the youth academy before making his debut in 2005. Unlike Cristiano Ronaldo, Nani spent two complete seasons with Sporting, making 76 appearances and scoring 11 goals, before joining Manchester United in 2007.
In England, the winger showed glimpses of his true potential but was often cited to be very inconsistent. He spent eight seasons as a Manchester United player winning almost everything possible with the Red Devils and even conjuring up the Player of the Year award in 2011 before returning to Sporting on loan for the 2014-15 season.
A move to Fenerbahce in 2015 was followed by a move to Valencia and a third return to Sporting CP in 2018. Nani would spend just one more season at Lisbon before moving to the MLS to join Orlando City in 2019.
3. Paulo Futre
One of the all-time greatest players in the history of Portuguese football, Futre joined the Sporting Academy in 1975 at the age of 9. The winger impressed in years to come and made his debut eight years later.
A request for a pay rise denied at the end of his debut season saw Futre making the move to rivals FC Porto in 1984, after making 24 appearances for his boyhood club. Futre went on to represent Atletico Madrid, Benfica, Marseille, Reggiana, AC Milan, West Ham and Yokohama Flugels in a 15-year long professional career.
The winger is one among seven players to have represented the 'big three' of Portuguese football (FC Porto, Sporting CP, and Benfica) during their playing careers. He is also the youngest player in the history of Portuguese football to play for the national side.