æz mˈɪdəlsbɹə ˈɔːltɚnˌeɪɾᵻd bᵻtwˌiːn ðə pɹəmˈɪɹ lˈiːɡ ænd fˈɜːst dᵻvˈɪʒən, flˈɛmɪŋ ɹᵻmˈeɪnd ɐ kˈɑːnstənt ɪnðə sˈaɪd ænd æz pˈɑːɹt ʌv ɹˈɑːbsənz skwˈɑːd hiː wʌz ɔnðə lˈuːzɪŋ sˈaɪd ɪnðə lˈiːɡ kˈʌp fˈaɪnəlz ɪn nˈaɪntiːnhˈʌndɹɪd nˈaɪnti sˈɛvən ænd nˈaɪntiːnhˈʌndɹɪd nˈaɪnti ˈeɪt ænd ðɪ ˌɛfˈeɪ kˈʌp fˈaɪnəl ɪn nˈaɪntiːnhˈʌndɹɪd nˈaɪnti sˈɛvən.
As Middlesbrough alternated between the Premier League and First division, Fleming remained a constant in the side and as part of Robson's squad he was on the losing side in the League Cup finals in 1997 and 1998 and the FA Cup final in 1997.