Nakamura played his debut Champions League game on 13 September against Manchester United at Old Trafford. He scored from a free kick to bring the game level at 2–2, making him the first Japanese footballer to score a goal in the Champions League, although Celtic eventually lost 3–2. On 14 October, in a league game against Dundee United at Tannadice, Nakamura scored the first hat-trick of his Celtic career and won the Man of the Match award; the game ended 4–1 in Celtic's favour. On 21 November, Nakamura scored perhaps the most important goal of his career with a 30-yard free kick against Manchester United at Celtic Park in a crucial Champions League game, leading to Celtic qualifying for the Champions League knockout stage for the first time. Sky Sports pundit and Southampton legend Matt Le Tissier later ranked Nakamura's free kick as among the best five set-piece goals he has ever seen. On 26 December, Nakamura chipped the ball over Dundee United's goalkeeper Derek Stillie at Celtic Park; the goal earned Nakamura the SPL Goal of the Season award. It was Nakamura's performance in the final 20 minutes of the game which allowed Celtic to escape with a point, prompting Gordon Strachan to proclaim him "a genius". On 25 February, during the Scottish Cup quarter-final between Celtic and Inverness Caledonian Thistle, Nakamura broke a bone in his left hand after an Inverness player stepped on it. Nevertheless, Nakamura played in the next game on 3 March against Dunfermline Athletic. Hoops manager Gordon Strachan insisted that Celtic couldn't play the second leg of the Champions League match against A.C. Milan in the San Siro without him. He played in both legs of the fixture, the first of which was a 0–0 draw at Celtic Park, with Milan going on to win the tie 1–0 after extra-time at the San Siro. On 22 April, Celtic won their 41st league championship, and second in a row. The title was won in dramatic fashion by an injury time free kick from Nakamura in a 2–1 victory against Kilmarnock. The result left Celtic 13 points clear of Rangers with four matches remaining. Quite fittingly, later that day Nakamura was recognised by his peers with the Scottish Player of the Year award. This was followed in May with the SFWA Footballer of the Year award and both Players' Player of the Year award and the