Hearts of Oak were left heart-broken as they went down 1-0 to Medeama on Wednesday in the Premier League.
Playing at their adopted home in Cape Coast following the temporary closure of the Accra Stadium, the Phobians were stunned when Kabiru Imoro grabbed a second half winner for the Mauves.
The defeat dents Hearts' hopes of piling the pressure on rivals, Asante Kotoko who are leading the standings.
With fans of the Club still agitating over the dismissal of coach David Duncan last week, the loss will further heighten the tension in their camp.
In Bechem, home side Bechem United posted a 3-2 victory over Heart of Lions.
Toufiq Sani and Samuel Yeboah grabbed two goals apiece for either side before Emmanuel Asante scored to wrap up victory for Bechem.
At the Wa Park, Berekum Chelsea shared the spoils with Wa All Stars in a goalless drawn game.