[['result', 'no', 'date', 'category', 'tournament', 'surface', 'opponent', 'score'], ['winner', '1', '15 july 2002', '250 series', 'stuttgart open , germany', 'clay', 'guillermo cañas ( arg )', '6 - 3 , 3 - 6 , 3 - 6 , 6 - 4 , 6 - 4'], ['runner - up', '1', '28 october 2002', '250 series', 'st petersburg open , russia', 'hard (i)', 'sébastien grosjean ( fra )', '5 - 7 , 4 - 6'], ['runner - up', '2', '20 september 2004', '250 series', 'china open , china', 'hard', 'marat safin ( rus )', '6 - 7 (4 - 7) , 5 - 7'], ['winner', '2', '25 october 2004', '250 series', 'st petersburg open , russia', 'carpet (i)', 'karol beck ( svk )', '6 - 2 , 6 - 2'], ['winner', '3', '19 february 2007', '500 series', 'rotterdam open , netherlands', 'hard (i)', 'ivan ljubičić ( cro )', '6 - 2 , 6 - 4'], ['runner - up', '3', '3 march 2007', '500 series', 'dubai tennis championships , united arab emirates', 'hard', 'roger federer ( sui )', '4 - 6 , 3 - 6'], ['winner', '4', '6 january 2008', '250 series', 'chennai open , india', 'hard', 'rafael nadal ( esp )', '6 - 0 , 6 - 1'], ['runner - up', '6', '11 october 2009', '500 series', 'rakuten japan open tennis championships , japan', 'hard', 'jo - wilfried tsonga ( fra )', '3 - 6 , 3 - 6'], ['winner', '5', '25 october 2009', '250 series', 'kremlin cup , russia', 'hard (i)', 'janko tipsarević ( srb )', '6 - 7 (5 - 7) , 6 - 0 , 6 - 4'], ['runner - up', '7', '8 november 2009', '500 series', 'valencia open 500 , spain', 'hard (i)', 'andy murray ( gbr )', '3 - 6 , 2 - 6'], ['runner - up', '8', '14 february 2010', '500 series', 'rotterdam open , netherlands', 'hard (i)', 'robin söderling ( swe )', '4 - 6 , 0 - 2 , ret'], ['runner - up', '9', '28 february 2010', '500 series', 'dubai tennis championships , united arab emirates', 'hard', 'novak djokovic ( srb )', '5 - 7 , 7 - 5 , 3 - 6'], ['winner', '7', '3 october 2010', '250 series', 'malaysian open , malaysia', 'hard (i)', 'andrey golubev ( kaz )', '6 - 7 (2 - 7) , 6 - 2 , 7 - 6 (7 - 3)'], ['runner - up', '10', '31 october 2010', '250 series', 'st petersburg open , russia', 'hard (i)', 'mikhail kukushkin ( kaz )', '3 - 6 , 6 - 7 (2 - 7)'], ['winner', '8', '5 february 2012', '250 series', 'zagreb indoors , croatia', 'hard (i)', 'lukáš lacko ( svk )', '6 - 2 , 6 - 3'], ['runner - up', '11', '16 june 2013', '250 series', 'gerry weber open , germany', 'grass', 'roger federer ( sui )', '7 - 6 (7 - 5) , 3 - 6 , 4 - 6'], ['winner', '9', '28 july 2013', '250 series', 'swiss open , switzerland', 'clay', 'robin haase ( nld )', '6 - 3 , 6 - 4']]
19 February 2007 is the earliest date in the 500 Series Category
[ENT] is the earliest date in the [ENT] [ENT]