During the 2006–07 season, he was twice sent on loan to AFC Bournemouth, at the same time as Chelsea teammate Jack Cork.
 He suffered a ruptured spleen in a youth team match against Arsenal that ruled him out of the later part of that season.

In August 2007, Bertrand joined Oldham Athletic on loan until January 2008.

On 4 January 2008, a matter of days after his spell at Oldham came to an end, Bertrand joined Norwich City on loan for the rest of the 2007–08 season.
He put in a number of impressive displays playing at both left full back and on the left wing, and admitted he would welcome a longer stay with the club.
Bertrand became popular with the Carrow Road crowd earning him the nickname 'Plastic' in reference to the Belgian singer Plastic Bertrand.
On 4 July 2008, he rejoined the club on loan until January 2009, with an option to extend to the end of the season.

On 17 July 2009, Bertrand joined Reading on a season-long loan.
He scored his first professional goal against Derby County on 10 March 2010.
He came third in the voting for Reading's player of the season, behind Gylfi Sigurðsson and Jimmy Kébé.

On 5 August 2010, Bertrand signed on loan with Championship club Nottingham Forest in an initial six-month deal.
He made his debut for Forest as a substitute in a 1–0 away defeat against Burnley.
He was a regular for Forest for whom he made a total of 19 appearances.
Forest were interested in either extending Bertrand's loan spell for the rest of the season or to sign him permanently but when his loan period expired on 3 January 2011 he returned to his parent club Chelsea.
During the 2006–07 season, he was twice sent on loan to AFC Bournemouth, at the same time as Chelsea teammate Jack Cork.  He suffered a ruptured spleen in a youth team match against Arsenal that ruled him out of the later part of that season.
In August 2007, Bertrand joined Oldham Athletic on loan until January 2008.
On 4 January 2008, a matter of days after his spell at Oldham came to an end, Bertrand joined Norwich City on loan for the rest of the 2007–08 season. He put in a number of impressive displays playing at both left full back and on the left wing, and admitted he would welcome a longer stay with the club. Bertrand became popular with the Carrow Road crowd earning him the nickname 'Plastic' in reference to the Belgian singer Plastic Bertrand. On 4 July 2008, he rejoined the club on loan until January 2009, with an option to extend to the end of the season.
On 17 July 2009, Bertrand joined Reading on a season-long loan. He scored his first professional goal against Derby County on 10 March 2010. He came third in the voting for Reading's player of the season, behind Gylfi Sigurðsson and Jimmy Kébé.
On 5 August 2010, Bertrand signed on loan with Championship club Nottingham Forest in an initial six-month deal. He made his debut for Forest as a substitute in a 1–0 away defeat against Burnley. He was a regular for Forest for whom he made a total of 19 appearances. Forest were interested in either extending Bertrand's loan spell for the rest of the season or to sign him permanently but when his loan period expired on 3 January 2011 he returned to his parent club Chelsea.
Ryan Bertrand