On 25 July 2009, Manolev signed a 3+2 years contract with the Dutch club PSV Eindhoven,[2] to fend competitions from Aston Villa.

He was selected as a starter against Bulgarian club Cherno More in the UEFA Europa League 3rd qualification round.

He played 69 minutes before being substituted for Jan Kromkamp, assisting Balázs Dzsudzsák's equalizing goal and earning himself a booking.

[5] On 23 August 2009, Manolev had another fine display, assisting two PSV goals in the 3–1 home win against NAC Breda.

[7] In the summer transfer window in 2012, Manolev was linked around Europe, with VfB Stuttgart[8] and Sporting Lisbon.

[9] Subsequently, his performance at PSV led to him being branded as "the worst right back in Europe" by RTL pundits, such as René van der Gijp, having become his outspoken critics since his arrival.

"[11] Upon his loan spell ended from Fulham, having lost a first team place to Santiago Arias and Joshua Brenet.

[14] After a failed move in the summer transfer window, Manolev was then sent to the reserve team and went on to make ten appearances, scoring once.

[19] Manolev made five league appearances and returned to PSV despite hopes of joining Fulham on a permanent basis.

He was subsequently banned for 5 matches, but on appeal the punishment for racism was dropped, with the player instead ordered to serve a 3-match suspension for general insults directed at the opponent.

Manolev was a part of the Bulgaria national football team in the World Cup 2010 qualifiers against Italy and Montenegro, but remained an unused substitute.