Welsh International Roy Paul has the rare distinction of captaining a winning side in all 13 rounds (as it was in his time) of the FA Cup competition.
There are several possible sequences but the one I have chosen starts with Worcester City in 1957/58 (Preliminary Round and then Qualifying Rounds 1 to 4) & 1958/59 (Rounds 1 to 3) and Manchester City in 1955/56 (Round 4 to Final).
This inevitably leads to the question can any player equal or come close to Roy’s record?
There will be probably be winning captains from the early days of the competition but in the post-war years it would need exceptional circumstances. However, I did wonder about another Manchester City captain Tony Book. Tony had a long non-league career before joining Manchester City. I believe he was captain of Bath City for a time and before signing for them was at Frome Town. Simply looking at the records of those three clubs here is a possible sequence for Tony Book although I do not know if he actually played/captained in the Frome Town/Bath City matches.
1955/56 Preliminary Round Frome Town beat Trowbridge Town 1957/58 First Qualifying Round Bath City beat Weston Super Mare 1957/58 Second Qualifying Round Bath City beat Clevedon 1957/58 Third Qualifying Round Bath City beat Glastonbury 1957/58 Fourth Qualifying Round Bath City beat Barry Town 1957/58 First Round Bath City beat Exeter City 1959/60 Second Round Bath City beat Notts County 1968/69 Third Round Manchester City beat Luton Town 1968/69 Fourth Round Manchester City beat Newcastle United 1968/69 Fifth Round Manchester City beat Blackburn Rovers 1968/69 Sixth Round Manchester City beat Tottenham Hotspur 1968/69 Semi Final Manchester City beat Everton 1968/69 Final Manchester City beat Leicester City