The two traditional clubs have won the clubs' competition ten times between them and are pooled together again to battle for supremacy in one of the matches of this round
The highlights of the draw was the pitching of two traditional teams - Shooting Stars Sports Club of Ibadan against Enyimba of Aba to vie for one of the eight slots to the quarter finals.
The two teams will do battle in Abuja.
Both teams have won the competition for a combined 10 times. Enyimba won the Federation Cup twice in 2005 and 2009 while 3SC are the record winners of the oldest club competition in Nigeria with eight victories.
The Oluyole Warriors won their first in 1959 then as Ibadan Lions and they followed that up with seven other titles in 1961, 1966, 1969, 1971 (as WNDC Ibadan) and the last three in 1977, 1979 and 1995 were won with their present name 3SC.
Despite their lack of titles in recent times, this tie will definitely be the talking point of the Round of 16 when they are played next Wednesday across Nigeria.
There are other mouth watering ties as Heartland who have won the last two Federation Cup competitions square up against Sharks of Port Harcourt who are seeking their first title after two losses in the final in 2003 and 2009 to Lobi Stars and Enyimba respectively.
Full Round of 16 Fixtures
Enyimba vs Shooting Stars - Abuja
Heartland vs Sharks - Benin
Akwa United vs Enugu Rangers -Owerri
Niger Tornadoes vs Warri Wolves - Akure
Kano Pillars vs Gombe United - Jos
Nasarawa United vs Sunshine Stars - Lokoja
Akwa Starlets vs Abia Warriors - Calabar
ABS vs Lobi Stars - Minna