During his first season at Bramall Lane Flynn established himself as first team player despite competing with the likes of Republic of Ireland International Stephen Quinn for a place in the starting eleven.
Selama musim pertamanya di Bramall Lane Flynn menjadikan dirinya sebagai pemain tim utama meski bersaing dengan orang-orang seperti Republik Irlandia Internasional Stephen Quinn untuk mendapatkan tempat di starting eleven.