 Nyorai mberi kweiyi ndima - Pakati pegore ra2013, zvakaziviswa kuti Carlo Ancelotti aizove murairidzi mukuru weReal Madrid mwaka wa2013-14. Real Madrid yakatanga mwaka nekukunda Real Betis ne2 uye 1 umo Casillas akaiswa pabhenji zvakare. Akaita kutanga kwake kwekutanga mumazuva 238 mumutambo weChampions League group stage neGalatasaray, asi akakuvara muminiti yechi14 mushure mekunge Sergio Ramos amubata nechiuno chisina kurongeka sezvo muchengeti wepagedhi akauya kubva pamutsetse wake kuti aite tsika yekubata. Pasinei nokuva muchengeti wechipiri wechikwata muLa Liga, shure kwaDiego López, Casillas akaramba ari muchengeti wekutanga weMadrid muChampions League neCopa del Rey, achiisa rekodhi itsva yemaminitsi 962 asina kugamuchira chinangwa mumakwikwi ekupedzisira. MunaFebruary 2014, akazova muchengeti wepagedhi wekutanga kutamba mumutambo wese weCopa del Rey pamberi pekupedzisira pasina kubvuma chinangwa. Musi wa 16 Kubvumbi, akatungamira Madrid mumutambo wekupedzisira pavakakunda vakwikwidzi veBarcelona 2 × 1 kuValencias Mestalla Stadium. Musi wa 24 May 2014, Casillas akatungamirira Real Madrid mu 2014 Champions League yekupedzisira, akahwina mukombe kechitatu mubasa rake nekukunda 4-1 pamusoro peAtlético Madrid muLisbon; iyi yaive nguva yegumi Real Madrid yakakunda mukombe. Kunyange zvazvo Diego Godíns opening goal yakakonzerwa nekukanganisa kwaCasillas, Sergio Ramos akafananidza mutambo weReal Madrid munguva yekukuvara; kirabhu yakaenderera mberi kuhwina zita munguva yekuwedzera. 