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I was granted Tier 2 visa in 2014 and due to the revocation of my employer’s sponsorship, my family had to apply for FLRO - FP - 7years route (when 4 years) visa in 2015 March. The history of my visa application as below.

FLRO - FP refused in Dec 2015
Appealed within 14 days in Dec 2015
Decision of 1st tribunal in May 2018
Reason for the Decision - refused as my son is not entitled for 7 years route as he was only 4 years.

Appealed to Upper Tribunal in May 2018
Decision for UT in July 2018
Reason for refusal - Refused the appeal/not admitted your application to appeal to the Upper Tribunal.

New application - FLRO - FP in Aug 2018 (applied within 14 days of UT decision)
Visa granted in May 2019.

Now I want to apply for settlement under ILR - Long Stay - 10 year route

Now my question is
1. Do I break the 10 year route as my Upper Tribunal appeal was refused as listed above?

No there is no break. You had section 3C until you exhausted your appeal rights. Then you applied within 14 days of becoming an overstayer and regularised your stay again. Such a period is discarded as per paragraph 39E of the rules.
The case law is also on your side: indefinite-leave-to-remain/ilr-10-years ... l#p1953365

THank you so much