Well, Willian almost always played as the RWF for Chelsea, and in that position he's certainly number 2 in Chelsea's history behind Cooke, and he could also act as backup for the LWF and AMF positions if needed. So I can understand why he's here even if he was never really a standout player, he was very hard working defensively, versatile and a good "servant" to the club despite sometimes frustrating the fans with his inconsistent attacking contribution.
I use the same formation in game, it's the best way to fit in all the biggest legends of the club. Osgood is the biggest legend pre-90s, even more than Bonetti and Harris, so it's good he's in the starting XI. Some older fans would even now say he's the best player in the club's history.
I think even if you're not going to include Azpilicueta over Sillett because of the latter's exceptional quality (I won't go back over that topic), then he must be here over McCreadie. While McCreadie had some very good attacking abilities for that era he wasn't anything outstanding in quality. And LB was actually the position that Azpilicueta started getting recognition for and he was exceptional in that position when they won the league in the 14/15 season. And of course his achievements with the club absolutely dwarf McCreadie's.
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I would also suggest Courtois over Cudicini in reserves, he was the main keeper for two League titles and two cups. Whereas Cudicini played as back-up for Čech for most of his stint at the club
I disagree, Cudicini is well loved by fans and Courtois is hated. It also seems to have been forgotten now, but Courtois wasn't even that good for Chelsea, and in fact he was criticised very often. A lot of fans even thought at the time they made the wrong decision letting Čech go because Courtois didn't play that well.
One player I would have tried to fit in the reserves is Tommy Law, he was a one club man and an important player for Chelsea in the 30s.