RANK

PLAYER

TROPHIES

WINNING YEARS

1

Lloyd Isgrove

3

Peterborough (2013-14), Barnsley (2015-16), Bolton Wanderers (2022-23)

2

Steve Phillips

2

Bristol City  (2002-03), Crewe Alexandra (2012-13)

3

Sam Ricketts

2

Swansea (2005-06), Coventry City, (2016-17)

4

Gregor Robertson

2

Chesterfield (2011-12), Crewe Alexandra (2012-13)

5

Mark Little

2

Peterborough  (2013-14), Bristol City (2014-15)

6

Michael Bostwick

2

Peterborough (2013-14), Lincoln (2017-18)

7

Josh Scowen

2

Barnsley (2015-16), Sunderland (2020-21)

8

Jordan Turnbull

2

Coventry City (2016-17), Salford (2019-20)

9

Lee Burge

2

Coventry City (2016-17), Sunderland (2020-21)

10

Jordan Willis

2

Coventry City (2016-17), Sunderland (2020-21)

11

Josh Vickers

2

Lincoln City (2017-18), Rotherham (2021-22)

12

Will Grigg

2

Sunderland (2020-21), Rotherham (2021-22)

13

Kieran Sadlier

2

Rotherham (2021-22), Bolton Wanderers (2022-23)

14

Jed Steer

2

Peterborough (2023-24, 2024-25)

15

Archie Collins

2

Peterborough (2023-24, 2024-25)

16

David Ajiboye

2

Peterborough (2023-24, 2024-25)

17

Ryan De Havilland

2

Peterborough (2023-24, 2024-25)

18

Joel Randall

2

Peterborough (2023-24, 2024-25)

19

Hector Kyprianou

2

Peterborough (2023-24, 2024-25)

20

Jadel Katongo

2

Peterborough (2023-24, 2024-25)

21

Ricky-Jade Jones

2

Peterborough (2023-24, 2024-25)

22

Kwame Poku

2

Peterborough (2023-24, 2024-25)

23

Nicholas Bilakapic

2

Peterborough (2023-24, 2024-25)

24

Malik Mothersille

2

Peterborough (2023-24, 2024-25)

25

Emmanuel Fernandez

2

Peterborough (2023-24, 2024-25)

26

Donay O'Brien-Brady

2

Peterborough (2023-24, 2024-25)

27

James Dornelly

2

Peterborough (2023-24, 2024-25)

28

Harley Mills

2

Peterborough (2023-24, 2024-25)