She was descendant of the influential American broodmare Best In Show, the ancestor of numerous major winners including El Gran Senor, Try My Best, Xaar, Jazil, Rags to Riches and Redoute's Choice.

On 4 September over the same distance at Salisbury Racecourse he started 11/10 favourite for a minor event and recorded his first victory as he drew right away from his opponents to win "readily" by nine lengths.

On his first appearance as a three-year-old Cityscape ran in the Greenham Stakes (a major trial race for the 2000 Guineas) at Newbury Racecourse on 18 April and finished second to the Irish-trained favourite Vocalised.

[6] After an absence of almost a year, Cityscape returned in a handicap race at Newbury on 17 April 2010 in which he was ridden by Jimmy Fortune and finished well to take fourth place.

Eleven days later he was partnered by Ryan Moore in the Listed Paradise Stakes at Ascot when he started the 4/9 favourite but was beaten into second place by the six-year-old gelding King of Dixie.

He was then sent to France for a very strong renewal of the Prix Jacques Le Marois at Deauville Racecourse on 15 August and came home eighth of the twelve runners in a race won by Immortal Verse.

[9] Less than two weeks after his win in Ireland Cityscape was shipped to Italy for the Group 1 Premio Vittorio di Capua at San Siro Racecourse in Milan.

[10] For his final appearance of the season Cityscape was sent to Sha Tin Racecourse to contest the Hong Kong Mile on 11 December and started a 32/1 outsider in a fourteen-runner field.

After tracking the leaders Cityscape went to the front 500 metres from the finish and went clear of the field in the closing stages to win "comfortably" by four and a quarter lengths from Mutahadee in a course-record time of 1:48.65.

[13] In the Champions Mile in Hong Kong on 1 May Cityscape started the 6/5 favourite but after struggling to obtain a clear run in the straight he came home tenth of the sixteen runners behind Xtension.