 Leonard akatanga kutamba neClippers musi wa22 Gumiguru 2019, apo akaisa 30 points, 6 rebounds, uye 5 assists mukukunda 112102 paLos Angeles Lakers. Musi waGumiguru 24, akarekodha mapoinzi makumi maviri nerimwe uye akabatanidza basa-rakakwira mapfumbamwe anobatsira mukukunda 141 122 pamusoro peGolden State Warriors. Musi waZvita 11, Leonard akadzokera kuToronto kekutanga kubva paakabatana neClippers uye akasangana nekurumbidzwa uye kusimuka kubva kune vateereri asati awana mapoinzi makumi maviri nematatu uye achinyora matanhatu anobatsira mukukunda 11292 pamusoro peRaptors. Mazuva maviri gare gare, Leonard akawana 42 points pamwe chete ne11 rebounds mukukunda 124117 pamusoro peMinnesota Timberwolves. Yaiva nguva yokutanga munhoroondo yechikwata kuti vatambi vaviri vakapfuura mapoinzi makumi mana, sezvo waaitamba naye Paul George akawana mapoinzi makumi mana nematanhatu. Pazuva reKisimusi, maClippers nemaLakers vakasangana zvakare mumutambo waitarisirwa zvikuru, umo Leonard akaisa mapoinzi makumi matatu nemashanu pa11-ye-19 kupfura uye 12 rebounds kutungamira maClippers kuhwina 111 × 106 kukunda kunyangwe vachitevera neanosvika gumi nemashanu. Musi waNdira 14, 2020, Leonard akarova mwaka wakakwira 43 mapoinzi mumaminetsi makumi maviri nemapfumbamwe chete mukukunda 128 × 103 pamusoro peCleveland Cavaliers. Akatumidzwa zita reWestern Conference Player yeVhiki yemitambo yakatambwa kubva muna Ndira 13 kusvika 19. Musi waJanuary 24, Leonard akanyora basa rake rekutanga katatu-kaviri nemapoinzi makumi matatu nematatu, gumi rebounds, uye gumi anobatsira mukukunda 122 117 pamusoro peMiami Heat. Musi waFebruary 16, Leonard akatumidzwa zita reNBA All-Star Game MVP ye2020 NBA All-Star Game. 