Teenoso third favourite for the Lingfield Derby Trial in May. He took the lead five furlongs from the finish and stayed on well to win by three lengths from Shearwalk. When Lester Piggott, who had won the race eight times previously, elected to ride Teenoso in the Derby, the colt was strongly supported in the betting and started 9/2 favourite in a field of twenty-one runners. Racing on the heaviest ground seen at Epsom for many years, Teenoso was among the leaders from the start. Piggott sent the colt into the lead early in the straight and he was never in
Jon Lester and the Red Sox were eliminated. Lester finished the season 15–9 with a 3.41 ERA. He finished in the top 20 in strikeouts (11th), wins (10th) and ERA (17th). In the end of the 2011 season, Lester and two more starting pitchers were in a center of a controversy that told that the three (and sometimes more) drank alcohol during games. Many people hypothesized that this was part of the reason why the Red Sox went 7–20 in September and were eliminated on the last day of the season. Lester was the first to tell what really happened, and stressed