I've seen a few posts suggesting Jose is too cautious in "big games" or against "big managers" recently, but I started to wonder what that pattern looked like over his career to see if there is any long-term validity to that. I compiled Jose's record against (1) Pep, (2) Klopp, (3) Conte, (4) (of course) Wenger, and (5) Pochettino to see how he stacks up against them historically. I used only league results from Jose's Chelsea stints (2004-07 and 2013-15), Inter (2009-10), Real Madrid (2010-13), and of course this year to date. I've broken it up by opponent manager and the clubs each manager was in charge of at the time, plus win (and loss, to test the "playing it safe in big games" theory) percentages.

vs Guardiola:
Jose's club|Pep's club|Pl.|W|D|L|Win %|Loss % :--|:-- Madrid|Barcelona|4|1|1|2|25%|50% Man Utd|Man City|1|0|0|1|0%|100% |Total|5|1|1|3|20%|60%

vs Klopp:
Jose's club|Klopp's club|Pl.|W|D|L|Win %|Loss % :--|:-- Chelsea|Liverpool|1|0|0|1|0%|100% Man Utd|Liverpool|2|0|2|0|0%|0% |Total|3|0|2|1|0%|33%

vs Conte:
Jose's club|Conte's club|Pl.|W|D|L|Win %|Loss % :--|:-- Inter|Atalanta|1|0|1|0|0%|0% Man Utd|Chelsea|1|0|0|1|0%|100% |Total|2|0|1|1|0%|50%**

vs Pochettino:
Jose's club|Poch's club|Pl.|W|D|L|Win %|Loss % :--|:-- Madrid|Espanyol|4|4|0|0|100%|0% Chelsea|So'ton|2|2|0|0|100%|0% Chelsea|Spurs|4|1|1|2|25%|50% Man Utd|Spurs|1|1|0|0|100%|0% |Total|11|8|1|2|73%|18%

vs Wenger:
Jose's club|Wenger's club|Pl.|W|D|L|Win %|Loss % :--|:-- Chelsea|Arsenal|11|5|6|0|45%|0% Man Utd|Arsenal|1|0|1|0|0%|0% |Total|12|5|7|0|42%|0% | | | | | | | |Record in Total:|33|14|12|7|42%|21%

In total, Jose's win percentage is 42%, which isn't stellar, but when you consider the flip side (these managers have a combined 21% win percentage against Jose), it's pretty impressive. The notion that he plays it safe seems to be supported by the results, as he's drawn (12) nearly as many as he's won (14). Breaking it down by manager: Pep - It is commonly accepted that Pep has had Jose's number historically, but the head-to-head league results aren't as bad as they've been made out to be. Time will tell as both sides, while having the potential to be world-class, have gaping weaknesses that should be addressed in the summer. Klopp and Conte - Arguably the managers against whom Jose has struggled the most, although the sample size for both is small. It's probably too early to draw conclusions, but it should be interesting to see how this pattern holds up in the coming years. Poch - Mou has dominated him, although Poch has typically been in charge of weaker sides. Poch has only won twice, both since he's taken over Spurs, but Jose has tied and won the two most recent match-ups. Hopefully this trend continues when we travel to White Hart Lane.

All in all, Jose's record against these men is very impressive imo. His win % isn't outstanding but most top managers have sub-50% win % against other top managers. Both Conte and Klopp have proved a thorn in his side, but I think we'll see his record against both trend towards his average in the coming years. Here's hoping we improve his win % vs. Conte Saturday Sunday!

EDIT: Formatting