John Nicholson (four wins)
At the turn of the 20th century, Nicholson was the club secretary of Sheffield United for over 30 years. During that period, he undertook the managerial duties of the club as the club had no coach. He went on to preside over the most successful period in the history of Sheffield United as he lifted the FA Cup in 1899, 1902, 1915, and 1925. Despite not officially holding the title of a manager, Nicholson is arguably one of the best managers in early football history. 

Sir Alex Ferguson (five wins)
Manchester United's longest-serving boss won a staggering major 38 trophies while at the helm of the club. He reigned as the Red Devils head coach for 27 years and steered the club towards achieving football glory during this tenure. He first won the FA Cup in 1990 and went on to add four more to United's trophy cabinet before he decided to hang his boots. It is worth noting that Ferguson won 13 Premier League titles with Manchester United. The club has been on a decline ever since the larger-than-life football tactician departed but did manage to win the 2016 FA Cup under Louis van Gaal which was the Dutch man's only trophy during his tenure at the helm. United have only won one Europa League trophy under Portuguese tactician Jose Mourinho since then. The trophy had remained to be their last silverware until recently when they bagged the Carabao Cup title under Erik ten Hag.

George Ramsay (six wins)
Ramsay was the manager and secretary of Aston Villa in their most successful period during the late 19th century. He first began at the club as a player where he introduced revolutionary tactics before his career was cut short by injury and he moved into the managerial role in 185. He reached eight FA Cup finals as a manager and won six of them between 1887 and 1924. Aston Villa were also conquerors of England six times under Ramsay and he is believed to be the first manager in the football world to get remuneration for his work. 

Arsene Wenger (seven wins)
The French man is the most decorated manager in the FA Cup competition's history as he led Arsenal to bag seven of these titles. He was a pioneer in the English game and his great name will forever be associated with England's oldest trophy. His first FA Cup win was in 1998 while his last was in 2017, a year just before he decided to call it quits as the Gunners boss. Wenger is also the only manager in the history of the modern Premier League era to undergo all 38 matches without a defeat a feat that earned his Arsenal squad of 2003-2004 season the nickname ‘invincibles’. Arsenal had been on a spiral decline ever since he left the club but have now earned their first Champions League play after his exit thanks to tactics applied by manager Mikel Arteta who would have led the Gunners to Premier League triumph this season were it not been for a few slips in their final games. 

(Image: The Telegraph)