PSA: This was discussed on the list and the outcome was that it is not a bug. The OP misused the CATEGORY keyword in a way that has been deprecated since 2008. Here's a version of the OP's file that behaves as expected.
More details about the CATEGORY changes and the deprecation can be found at https://code.orgmode.org/bzg/org-mode/src/master/etc/ORG-NEWS#L1642 N.B. There are CATEGORY properties under each heading (and since property drawers are only recognized immediately after a heading (modulo scheduling information), the new headings are mandatory: --8<---------------cut here---------------start------------->8--- * the world cup on my agenda ** group stage :PROPERTIES: :CATEGORY: groups :END: %%(diary-block 6 22 2018 6 22 2018) 7:00 wc: brazil - costa rica (sans petersburgo){GE2} %%(diary-block 6 22 2018 6 22 2018) 10:00 wc: nigeria - islanda (volgogrado){GD2} %%(diary-block 6 22 2018 6 22 2018) 13:00 wc: serbia - suiza (kaliningrado){GE2} %%(diary-block 6 23 2018 6 23 2018) 07:00 wc: belgica - tunez (otkrytiye, moscu){GG2} %%(diary-block 6 23 2018 6 23 2018) 10:00 wc: mexico - korea (rostov){GF2} %%(diary-block 6 23 2018 6 23 2018) 13:00 wc: alemania - suecia (sochi){GF2} %%(diary-block 6 24 2018 6 24 2018) 07:00 wc: inglaterra - panama (nizhny){GG2} %%(diary-block 6 24 2018 6 24 2018) 10:00 wc: japon - senegal (ekaterimburgo){GH2} %%(diary-block 6 24 2018 6 24 2018) 13:00 wc: colombia - polonia (kazán){GH2} %%(diary-block 6 25 2018 6 25 2018) 09:00 wc: uruguay - rusia (samara){GA3} %%(diary-block 6 25 2018 6 25 2018) 09:00 wc: egipto - arabia (volgogrado){GA3} %%(diary-block 6 25 2018 6 25 2018) 13:00 wc: portugal - iran (saransk){GB3} %%(diary-block 6 25 2018 6 25 2018) 13:00 wc: espanha - marruecos (kaliningrado){GB3} %%(diary-block 6 26 2018 6 26 2018) 09:00 wc: Dinamarca - francia (luzhniki, moscu){GC3} %%(diary-block 6 26 2018 6 26 2018) 09:00 wc: PERÙ - australia (sochi){GC3} %%(diary-block 6 26 2018 6 26 2018) 13:00 wc: argentina - nigeria (san petersburgo){GD3} %%(diary-block 6 26 2018 6 26 2018) 13:00 wc: croacia - islandia (rostov){GD3} %%(diary-block 6 27 2018 6 27 2018) 09:00 wc: corea - alemania (kazán){GF3} %%(diary-block 6 27 2018 6 27 2018) 09:00 wc: mexico - suecia (ekaterimburgo){GF3} %%(diary-block 6 27 2018 6 27 2018) 13:00 wc: brazil - serbia (otkrytiye, moscu){GE3} %%(diary-block 6 27 2018 6 27 2018) 13:00 wc: suiza - costa rica (nizhny){GE3} %%(diary-block 6 28 2018 6 28 2018) 09:00 wc: polonia - japon (volgogrado){GH3} %%(diary-block 6 28 2018 6 28 2018) 09:00 wc: colombia - senegal (samara){GH3} %%(diary-block 6 28 2018 6 28 2018) 13:00 wc: inglaterra - belgica (kaliningrado){GG3} %%(diary-block 6 28 2018 6 28 2018) 13:00 wc: panama - tunez (saransk){GG3} ** 16 :PROPERTIES: :CATEGORY: 8 :END: %%(diary-block 6 30 2018 6 30 2018) 09:00 wc: 1cFrancia - 2dArgentina (kazán){16} %%(diary-block 6 30 2018 6 30 2018) 13:00 wc: 1aUruguay -2bPortugal (sochi){16} %%(diary-block 7 01 2018 7 01 2018) 09:00 wc: 2aRusia - 1bEspaña (moscu){16} %%(diary-block 7 01 2018 7 01 2018) 13:00 wc: 2cDinamarca - 1dCroacia (nizhny){16} %%(diary-block 7 02 2018 7 02 2018) 09:00 wc: 1eBrazil - 2fMexico (samara){16} %%(diary-block 7 02 2018 7 02 2018) 13:00 wc: 1gBelgica - 2hJapon (rostov){16} %%(diary-block 7 03 2018 7 03 2018) 09:00 wc: 2eSuiza - 1fSuecia (san petersburgo){16} %%(diary-block 7 03 2018 7 03 2018) 13:00 wc: 2gInglaterra - 1hColombia (moscu){16} ** 8 :PROPERTIES: :CATEGORY: 4 :END: %%(diary-block 7 06 2018 7 06 2018) 09:00 wc: 1qfFrancia - 2qfUruguay (nizhny){4} %%(diary-block 7 06 2018 7 06 2018) 13:00 wc: 5qfBrasil - 6qfBelgica (kazán){4} %%(diary-block 7 07 2018 7 07 2018) 09:00 wc: 7qfRusia - 8qfCrocia (samara){4} %%(diary-block 7 07 2018 7 07 2018) 13:00 wc: 3qfSuecia - 4qfInglaterra (sochi){4} ** Semifinal :PROPERTIES: :CATEGORY: semi-final :END: %%(diary-block 7 10 2018 7 10 2018) 09:00 wc: 1sf - 2sf (san petersburgo){SF} %%(diary-block 7 11 2018 7 11 2018) 09:00 wc: 3sf - 4sf (moscu){SF} ** Final :PROPERTIES: :CATEGORY: final :END: %%(diary-block 7 14 2018 7 14 2018) 09:00 wc: 1p - 2p (san petersburgo){F} %%(diary-block 7 15 2018 7 15 2018) 09:00 wc: 1f - 2f (luzhniki, moscu){F} --8<---------------cut here---------------end--------------->8--- -- Nick "There are only two hard problems in computer science: cache invalidation, naming things, and off-by-one errors." -Martin Fowler