Liberty Professionals have been eliminated from the MTN FA Cup competition after losing 1-2 to Samartex at the Carl Reindoff Stadium in Dansoman.
Liberty were however not the only topflight side to be knocked out as third tier side Afienya City beat Great Olympics 5-4 on penalties in the round of 32 matches played on Sunday.
Inter Allies also survived a near scare as they managed a 3-1 win over Division One side Proud United during penalties after a 1-1 scoreline at fulltime.
At the Tarkwa T&A Park, Medeama beat Goldstars 3-0 during penalties after a goalless game.
In other matches played on Sunday, Aduana beat Susubribi 3-5 at penalties as Mighty Jets booked a place in the round of 16 after beating Bofoakwa away at the Sunyani Stadium.
However Premier League leaders Ashantigold thumped Starke FC 3-0 at the Len Clay Stadium to qualify into the next stage.
Below are the full results of matches played on Sunday:
Afienya City 2(5-4)2 Great Olympics
Susubribi 1(3-5)1 Aduana Stars
77 Stars 1-5 Istanbul
Ashantigold 3-0 WA African United
Tamale Utrecht 2-0 Starke FC
Bofoakwa 1(2-4) 1 Mighty Jets
Liberty Prof. 1-2 Samartex
Proud United 1(1-3)1 Inter Allies
Medeama 0(3-0)0 Gold Stars