RANK

PLAYER

TROPHIES

WINNING YEARS

1

Ally McCoist

9

Rangers (1983-84, 1984-85, 1986-87, 1987-88, 1988-89, 1990-91, 1992-93, 1993-94, 1996-97)

2

Davie Cooper

8

Rangers (1977-78, 1978-79, 1981-82, 1983-84, 1984-85, 1986-87, 1987-88, 1988-89)

3

James Forrest

8

Celtic (2014-15, 2016-17, 2017-18, 2018-19, 2019-20, 2021-22, 2022-23, 2024-25)

4

Callum McGregor

8

Celtic (2014-15, 2016-17, 2017-18, 2018-19, 2019-20, 2021-22, 2022-23, 2024-25)

5

Scott Brown

7

Hibernian  (2006-07), Celtic (2008-09, 2014-15, 2016-17, 2017-18, 2018-19, 2019-20)

6

Billy McNeill

6

Celtic (1965-66, 1966-67, 1967-78, 1968-69, 1969-70, 1974-75)

7

Bobby Lennox

6

Celtic (1965-66, 1966-67, 1967-78, 1968-69, 1969-70, 1974-75)

8

Leigh Griffiths

6

Celtic (2014-15, 2016-17, 2017-18, 2018-19, 2019-20, 2021-22)