Rubuta ci gaba ga wannan sakin layi - Da yake gaskanta Pettitte ya zama mafi kyawun kwallo, Yankees sun yi musayar Hitchcock kafin kakar wasa ta 1996. Fara kakar wasa a cikin juyawa, Pettitte yana da rikodin 13<unk>4 a ƙarshen rabin farkon kakar, kuma ya sanya AL All-Star team. Bai bayyana a cikin MLB All-Star Game na 1996 ba, saboda ciwon hannu. Ya jagoranci AL tare da nasara 21 kuma ya gama na uku a cikin nasara nasara (.724), kuma na takwas a ERA (3.87). Ya gama na biyu ga Pat Hentgen don AL Cy Young Award, tare da mafi ƙarancin bambanci a cikin jefa ƙuri'a tun 1972. Hentgen ya lashe kyautar a wani bangare saboda ya jefa wasannin da suka fi Pettitte. Yankees sun ci Texas Rangers a 1996 ALDS da Baltimore Orioles a cikin 1996 American League Championship Series
(ALCS) da kuma Pettitte ya lashe wasanni biyu a kan Orioles, kuma yana da damarsa na uku a cikin jerin da aka soke ta ruwan sama. Pettitte ya fara wasa na 1 na Wasannin Duniya na 1996 da Atlanta Braves. Ya ba da izinin gudu bakwai a cikin wasan farko a wasan farko, amma ya ci John Smoltz a wasan 5, wanda Yankees suka ci 1 <unk> 0. Yankees sun ci Braves a wasa na shida don lashe jerin, wasanni hudu zuwa biyu.