Could someone help me understand or rather provide a comparison between using winstone vs tomcat from both functionality perspective as well as performance perspective.
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Winstone is an old servlet-container. It is not maintained anymore (last release was in January 2008) and only supports servlet api 2.5. As a feature comparison, Tomcat supports servlet api 3.1 (and support of servlet api 4.0 is on the way). Tomcat is the most used servlet container in the world and well maintained.
For performance comparison between Tomcat and Winstone, I do not know of a benchmark but I would put trust in the most used and tested (ie Tomcat).
Between Tomcat and Winstone, the choice is fast.
Note: Winstone was known to be a lightweight servlet container embedded in Jenkins. But Jenkins has replaced it by embedded Jetty a long time ago.