John Tait"Jacky" Robertson                 All of Chelsea Fc managers

                  In April 1905, Robertson was the first player to be signed by the newly formed Chelsea Football Club, but continued to play as well. It was                         Robertson who scored Chelsea's first competitive goal, in a 1–0 win at Blackpool on 9 September 1905. In his first season, he led the club to a                   third-place finish in the Second Division, one place off promotion. Robertson then surprisingly resigned from the club (third in the table at the time)                   on 27 November 1906. Chelsea were promoted to the top flight at the end of that season under                                                                                 caretaker secretary-manager William Lewis.

Jacky made a total of 39 apperances for chelsea with 36 of them in the First Division and he scored a total of 7 goals

Jacky's managing career only lasted one year at Chelsea, joining 1st April 1905 till his departure on 1st October                                                       1907 in that time John managed a total of 83 games winning 49, drawing 15 and losing 19, John had at his time                                                       at chelsea a 40.67% chance of winning.

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William Lewis

                   Lewis became the first club secretary of Chelsea when it was founded in 1905 and his contacts helped the club gain election to Football                            League the same year. With the resignation of player-manager John Robertson on 27 November 1906, Lewis became caretaker manager of                        the club, while retaining his secretarial duties. Lewis led the side to its first promotion in the 1906–07 season, finishing as Second                                      Division runners-up to Nottingham Forest. He left the job in June 1907 and was succeeded by David Calderhead.

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David Calderhead

                  Calderhead was Chelsea's first full-time secretary-manager and spent almost 26 years at the club, making him the club's longest-                           serving manager. In his time there, the team were relegated twice, in 1909–10 and subsequently re-promoted as Second                                   Division runners-up.

                  He took Chelsea to their first FA Cup final, in 1915, but in a match overshadowed by the First World War they were beaten                               by Sheffield United 0–3 at Old Trafford. The club later reached two more semi-finals under Calderhead and were on course for a                         domestic double in 1919–20 but ultimately finished 3rd in the First Division and were denied in the FA Cup by Aston Villa.

A second relegation ensued in 1923–24 before the side of Willie Ferguson, Tommy Law and Andy Wilson endured a succession of near misses before securing promotion in 1929–30.

Calderhead was notoriously shy of the media, earning the nickname "The Sphinx of Stamford Bridge". But he was not afraid to spend headline-making transfer fees on star strikers (especially fellow Scots), bringing the likes of Hughie Gallacher, Alex Jackson and Alec Cheyne to Stamford Bridge. Despite the glamour of the squad, trophies remained elusive. 1931–32 brought a further FA Cup semi final. Tommy Lang inspired Newcastle to a 2-goal lead and despite Gallacher pulling a goal back, Newcastle progressed to the final.

Calderhead holds the record at Chelsea for managing games – 966. He left the job in June 1933 to be replaced by Leslie Knighton. Calderhead died five years after leaving Chelsea in London at the age of 73.

His son, also called David, played for Chelsea while Calderhead was manager and later managed Lincoln City

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A Leslie Knighton

                        Leslie moved to Chelsea (1933–39) taking over from the long serving David Calderhead but didn't achieve anything at the club.

                        Out of the six seasons he managed his best was the 1935/36 season where Chelsea finished 8th with 43 points

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Billy Birrell

                         The 42-year-old tweeds-wearing, pipe-smoking Scot, Billy Birrell, arrived at Stamford Bridge from QPR on 19 April 1939 with ‘a reputation                          as one of the shrewdest and most capable managers in the game’ (Press Association). A native of Anstruther, Fife, and former player and                            manager at Raith Rovers, he took over one of the most attractive offices in the game but as the club’s first manager exclusively (Harold                                  Palmer, son of former assistant secretary Bert, stepped up from the assistant role to club secretary).