 Nyorai kuenderera mberi kweiyi ndima - Trippier akasainira La Liga kirabhu Atlético Madrid musi wa17 Chikunguru 2019 pachibvumirano chemakore matatu, pamubhadharo wemamiriyoni makumi maviri emadhora pamwe nekuwedzera. Akava mutambi wokutanga wechiNgezi weAtlético mumakore 95. Mukutanga kwake musi wa 18 Nyamavhuvhu mukutanga kwavo La Ligamumutambo wakanangana neGetafe, akabatsira timu kuhwina 1-0 kumba nekubatsira chinangwa chaÁlvaro Morata. Muna Zvita 2020, Trippier akapihwa 10-vhiki pasi rese nhabvu kurambidzwa uye faindi ye 70,000 yekutyora ina yeFootball Association kubheja mirau mushure mekunge anonzi apfuudza ruzivo nezve kutamisa kwake kushamwari dzake dzakazoisa kubheja pane kutamisa kwake. Kurambidzwa kwakamiswa neFIFA, iyo yakaramba kukwirira kwayo, kusvikira nyaya yacho yasarudzwa neDare reArbitration for Sport CAS. CAS yakaramba chikumbiro, uye Trippier akagara kunze kwekurambidzwa kwake kusvika paakadzokera kuchikwata cheMadrid Derby vachipesana neReal Madrid musi wa7 Kurume 2021, iyo yakapera mukukwikwidza 11. 