SQL Server 2019

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with tbl(person, EvaluationDate, Casescore) as(
      select 'Jane',	2012, -12 union all   
      select 'Hubert',	2014, -5 union all
      select 'Jane',	2020, -5 union all
      select 'Jane',	2015, +16 union all
      select 'Hubert',	2011, -100
), t as (
   select Person, EvaluationDate, Casescore,
       row_number() over(partition by Person order by EvaluationDate) rn
   from tbl 
), rq as (
   select *,
       case when 100 + Casescore < 0   then 0
            when 100 + Casescore > 100 then 100
            else 100 + Casescore end CumulativeScore
   from t
   where rn = 1
   
   union all 
   
   select t.Person, t.EvaluationDate, t.Casescore, t.rn,
       case when rq.CumulativeScore + t.Casescore < 0   then 0
            when rq.CumulativeScore + t.Casescore > 100 then 100
            else rq.CumulativeScore + t.Casescore end 
   from rq
   join t on t.rn = rq.rn + 1 and t.Person = rq.Person
)
select Person, EvaluationDate, Casescore, CumulativeScore
from rq
order by Person, EvaluationDate

Person	EvaluationDate	Casescore	CumulativeScore
Hubert	2011	-100	0
Hubert	2014	-5	0
Jane	2012	-12	88
Jane	2015	16	100
Jane	2020	-5	95