Obileye, 19, played the third game of his trial last night in the 1-0 win over Wrexham at the Racecourse Ground, with Chris Lester hitting the winner on 30 minutes.
The Hackney-born midfielder started his early career at the Leyton Orient Centre of Excellence, before being plucked to join Premier League giants Chelsea on schoolboy terms in 2011.
Following his release from Chelsea, he moved to Yorkshire, joining Sheffield Wednesday where he made speedy progress through their youth ranks. He would go on to make his professional debut on 30 August 2011, in the Football League Trophy 0-0 draw with Yorkshire rivals Bradford City at Valley Parade, which Bradford won on penalties following a goalless draw.
Obileye was made the Sheffield Wednesday Development Squad captain for the 2012-13 season and after a successful season was awarded by signing his first professional contract for the club, lasting one-year.
From all reports he played well last night, though with fierce midfield competition from Medo, Jay Spearing, Liam Trotter and Neil Danns it remains to be seen whether the 19 year old can make the grade at Wanderers.