Since arrangement of sheet music for orchestral ensemble requires a certain musical knowledge and expertise, amateur orchestral musicians often have difficulties when they arrange the sheet. An automatic arrangement method was proposed by employing Eigenmusic which is a set of eigenvector for many music excerpts, in order to evaluate the similarity among phrases. The difficulty in playing the arranged sheet music, however, was not evaluated so whether players feel difficulties on playing was out of discussion. This study proposes procedure for evaluating the degree how easy to play the phrases on sheet music. This procedure generates phrases for woodwind instruments using a MIDI database of backing phrases. Each musical phrases selected from the database are allocated to instrumentalists. Next, the ease of playing each phrases is evaluated based on fingering that is important in performance. Finally, phrases evaluated as the easiest are conjoined in each instrumentalist. We conducted an experiment to investigate the ease of playing for generated sheet music by musician’s rating. Experimental results showed that the procedure for evaluating ease of playing is effective so that proposed procedure can generate easier phrases to play than our previous method.