» May 26, 1911: In one of the few games in which both appear, Christy Mathewson and Grover Cleveland Alexander are relievers in a 5–3 win for the Giants over the Phillies. Matty takes over for Bugs Raymond in the 8th after the starter gives up two quick runs. With runners on 1B and 3B, Mickey Doolan flies to Devlin in right and his perfect strike to Chief Meyers is good for a DP. The Giant score to give Matty the win over Bill Burns, though by today's standards, it would be a save.
» August 6, 1912: Inspired in part by the Ty Cobb suspension and the Tigers' brief strike in May, the formation of a Players' Fraternity is announced, headed by attorney and former player Dave Fultz. Leading players include Cobb, Christy Mathewson, Mickey Doolan, and Jake Daubert. The goals are to oppose contract violations, rowdyism, and anything that may "impair a player's ability." At one point, a strike will be called for a Brooklyn attempt to send an obscure player, Harry Kraft, down to Newark, but many teams balk at the strike call, and it is rescinded.
» August 30, 1913: The Giants score six runs against Grover Cleveland Alexander, but the Phillies come back from the 6–0 deficit to score eight against Christy Mathewson. With two outs in the top of the 9th, and the Phils leading 8–6 over New York, umpire Bill Brennan, acceding to a request by the wily John McGraw, orders Phils captain Mickey Doolan (Phils manager Red Dooin had been ejected during the 6-run 6th) to have spectators removed from the CF bleachers, where they are waving hats, newspapers, and handkerchiefs to distract the batters. When Doolan refuses, Brennan forfeits the game, 9–0, to the Giants. Bedlam ensues and later, when the two umpires and Giants players try to board the train at the North Philadelphia Station, they are attacked by fans. The police draw their revolver to control the crowd. The Phils protest the forfeit and NL president Lynch will reverse the umpire and rule the game an 8–6 Phils win. The Giants then appeal. NL directors say both Brennan and Lynch are wrong, and order the game completed from the point at which it was stopped. The game will be finished October 2, with the outcome the same.
» February 10, 1916:
In a sweet deal, the Cubs send cash to the sinking Chicago Whales (Federal League) and bring back Three Finger Brown, Clem Clemens, Mickey Doolan, Bill Fischer, Max Flack, Claude Hendrix, Les Mann, Dykes Potter, Joe Tinker, Rollie Zeider, and George McConnell.
» August 28, 1916: The Giants send veteran Larry Doyle to the Cubs, along with Herb Hunter, for 3B Heinie Zimmerman and SS Mickey Doolan. The move allows Buck Herzog to shift to 2B.