 Nyorai kupfuurira kweiyi ndima - MunaNovember 1999, Overmars akarova hat-trick yake yekutanga yeArsenal, kumba kuMiddlesbrough. Kuita kwake kwakarumbidzwa nomutori wenhau Lynne Truss, uyo akanyora muThe Times, Overmars akanga ari pamusoro paJack Russell, achimhanya achitevera bhora uye akagadzirira kuparadza munhu upi noupi aiedza kuribvisa kwaari. Akapeta chigunwe chake mumutambo weArsenal vachipesana neSheffield Chitatu muna Ndira 2000 uye akange asiri mumutambo kwemavhiki matanhatu. Kusiyana nemwaka miviri yapfuura, Arsenal haina kumbobvira yaita kutyisidzira kwakakomba kuManchester United, iyo yakaenderera mberi nekuchengetedza ligi muna 1999 2000. Overmars akanga ataura pamberi pemushandirapamwe kuti Arsenal yakanga yakasimba sevadzivisi vavo, kunyanya pakurwisa kwatinenge tava nemamwe mazhinji. Arsenal yakapedza mwaka weligi zvine simba, ichikunda mitambo misere yakateedzana pakati paKurume naMay kuenda kubva pachinzvimbo chechishanu kuenda pachinzvimbo chechipiri. Muna Kubvumbi 2000, Overmars akarova zvibodzwa zvekukunda vachipesana naEverton uye ndiye aive mutambi akatanhamara mumutambo. Mutambo wake wokupedzisira weArsenal waiva 2000 UEFA Cup Finalvachipesana neGalatasaray, iyo yavakakundwa 41 pakurohwa mushure mekunge vasina kurova. 