Мы также можем использовать data.table
library(data.table)
setDT(df)[, Date := as.IDate(Date, "%m/%d/%Y")
][, monthly.running.sum := cumsum(score),format(Date, "%Y-%m")][]
# Date score monthly.running.sum
# 1: 2019-10-02 7 7
# 2: 2019-10-09 6 13
# 3: 2019-10-16 12 25
# 4: 2019-10-23 2 27
# 5: 2019-10-30 13 40
# 6: 2019-11-06 2 2
# 7: 2019-11-13 4 6
# 8: 2019-11-20 15 21
# 9: 2019-11-27 16 37
#10: 2019-12-04 4 4
#11: 2019-12-11 24 28
#12: 2019-12-18 28 56
#13: 2019-12-25 8 64
#14: 2020-01-01 1 1
#15: 2020-01-08 15 16
#16: 2020-01-15 9 25
#17: 2020-01-22 8 33
данные
df <- structure(list(Date = c("10/2/2019", "10/9/2019", "10/16/2019",
"10/23/2019", "10/30/2019", "11/6/2019", "11/13/2019", "11/20/2019",
"11/27/2019", "12/4/2019", "12/11/2019", "12/18/2019", "12/25/2019",
"1/1/2020", "1/8/2020", "1/15/2020", "1/22/2020"), score = c(7L,
6L, 12L, 2L, 13L, 2L, 4L, 15L, 16L, 4L, 24L, 28L, 8L, 1L, 15L,
9L, 8L)), row.names = c(NA, -17L), class = "data.frame")