Boyd joined Nottingham Forest on loan until the end of the 2010–11 season. Loan to Nottingham Forest Despite speculation during the January transfer window, Boyd remained at Middlesbrough and had not started a match for a month by the time the loan deal was signed, having only started 19 games the whole season for Middlesbrough. Boyd's loan deal was signed until the end of the 2010–11 season and Boyd was issued with the number 22 jersey. Nottingham Forest goalkeeper Paul Smith moved in the opposite direction because of injuries at Middlesbrough. The same day he made his move to Forest, Boyd debuted from the bench in a 2–1 defeat to Sheffield United. He scored six goals in ten league appearances for Forest, taking his total in the Football League Championship to twelve. Eskişehirspor Boyd signed a three-year contract with Turkish Süper Lig club Eskişehirspor on 8 July 2011. Boyd terminated his contract on 19 December 2011 and started legal proceedings against Eskişehirspor claiming he had never been paid during his stay at the club. He played just 76 minutes of league football for Eskişehirspor. Portland Timbers On 23 January 2012, Boyd declined a contract offer from Major League Soccer side Houston Dynamo. Boyd instead signed with Portland Timbers of MLS on 30 January 2012, becoming the club's second Designated Player. As Houston held exclusive rights within MLS to negotiate with Boyd, Portland were forced to trade a first-round pick in the 2013 MLS SuperDraft to the Dynamo for the right to sign him. Boyd scored his first goal for the Timbers on 4 March 2012 during a pre-season exhibition against AIK of Sweden. Eight days later, Boyd made his league debut in their season opener, where he scored Timbers' second goal of a 3–1 victory against Philadelphia Union. Boyd featured less frequently, however, after head coach John Spencer was fired. He scored seven goals in 26 appearances for Portland in the 2012 Major League Soccer season. On 31 January 2013, the Timbers announced that they had mutually agreed to end Boyd's contract. Kilmarnock (second spell) Boyd signed a short-term deal until the end of the 2012–13 season with Kilmarnock in February 2013. Boyd was given the number eleven shirt. In 2013–14, Boyd went on to have his most prolific season for Kilmarnock, scoring 22 goals in 37 matches. His success in front of goal garnered a Scotland recall and a