PluginsDir=plugins
FeaturesDir=features
PluginIDSeparator=_
RemovingScriptFileName=remove-old-eclipse-plugins.txt
rm -rf $RemovingScriptFileName

#for dir in $PluginsDir $FeaturesDir
for dir in $PluginsDir  # $FeaturesDir: most file names in features dir contains more than 1 _ character
do
    echo"Processing [$dir] directory..."
    # split PluginID from filename
    # (not reliable, but general working. (ex: will get one junit PluginID because there're move than 1 _ characters in file name))
    file_list=$(ls $dir);
    echo"$file_list" | cut -f1 -d $PluginIDSeparator         > $dir-all.txt
    echo"$file_list" | cut -f1 -d $PluginIDSeparator  | uniq > $dir-uniq.txt

    # get the PluginList which VERY POSSIBLY has old versions
    diff_result=$(diff -U 0 $dir-uniq.txt $dir-all.txt)
    plugins_which_has_old_versions=$(echo"$diff_result" | grep -e"^+[^+]" | cut -f 2 -d +)

    #
    for p in $(echo"$plugins_which_has_old_versions")
    do
        echo"$p"
        i=0
        for f in $(ls -d -t $dir/$p$PluginIDSeparator*) # use 'ls' command, can sort result by file time, but can not handle file name contains special characters (white space) when using wildcard
        #for f in $(find $dir -name"$p$PluginIDSeparator*")    # use 'find' command
        do
            if [ -d $f ]
            then
                # should use rm -rf
                echo -n"[D]"
            else
                echo -n"  "
            fi
            echo -n"$f"

            ((i++))
            if [ $i -eq 1 ]
            then
                echo""
                continue    # first file, the newest version
            fi
            echo"    [old]"
            echo"rm -rf $f">> $RemovingScriptFileName
        done

        echo
    done
done

org.junit
[D]plugins/org.junit_3.8.2.v3_8_2_v20100427-1100
[D]plugins/org.junit_4.8.2.v4_8_2_v20110321-1705    [old]  <-- wrong

$ ./guess-old-eclipse-plugins.sh
Processing [plugins] directory...
org.eclipse.gef
   plugins/org.eclipse.gef_3.7.2.v20111106-2020.jar
   plugins/org.eclipse.gef_3.6.2.v20110110-2020.jar    [old]

org.eclipse.help.base
   plugins/org.eclipse.help.base_3.6.2.v201202080800.jar
   plugins/org.eclipse.help.base_3.5.3.v201102101200.jar    [old]

org.eclipse.help.ui
   plugins/org.eclipse.help.ui_3.5.101.r37_20110819.jar
   plugins/org.eclipse.help.ui_3.5.3.r36_20101116.jar    [old]
...

rm -rf plugins/org.eclipse.gef_3.6.2.v20110110-2020.jar
rm -rf plugins/org.eclipse.help.base_3.5.3.v201102101200.jar
rm -rf plugins/org.eclipse.help.ui_3.5.3.r36_20101116.jar
rm -rf plugins/org.eclipse.help.webapp_3.5.3.r36_20101130.jar
rm -rf plugins/org.eclipse.jdt.apt.core_3.3.402.R36_v20110120-1000.jar
rm -rf plugins/org.eclipse.jdt.debug.ui_3.5.2.v20100928a_r362.jar

\[eclipse\]/dropins/eclemma1.3.1/eclipse/(plugins|features)

eclipse -application org.eclipse.equinox.p2.garbagecollector.application -profile epp.package.jee

# -*- coding: utf-8 -*-
import os
import re
from datetime import datetime

directory="C:\\eclipse64\\plugins"
dirBackup="C:\\eclipse64\\PluginsBackup"        #This folder is a kind of recycle bin for save deleted plugins. In case you have problems running eclipse after remove them you can restore them. If you don't detect any problem you can erase this folder to save disk space
manual=False    #Verifying deletion of each plugin manually (True) or automatic (False)

def globRegEx(directory,pat,absolutePath=True,type_=0):
    '''Function that given a directory and a regular pattern returns a list of files that meets the pattern

    :param str directory: Base path where we search for files that meet the pattern
    :param str pat: Regular expression that selected files must match
    :param bool absolutePath: Optional parameter that indicates if the returned list contains absolute (True) or relative paths (False)
    :param int type_: Type of selection 0: selects files and directories 1: only selects files 2: only selects directories
    :return: a list with the paths that meet the regular pattern
    '''
    names=os.listdir(directory)
    pat=re.compile(pat)
    res=[]

    for name in names:
        if pat.match(name):
            path=directory+os.sep+name

            if type_==1 and os.path.isfile(path):
                res.append(path if absolutePath else name)
            elif type_==2 and os.path.isdir(path):
                res.append(path if absolutePath else name)
            elif type_==0:
                res.append(path if absolutePath else name)

    return(res)

def processRepeated(repList):
    ''' this function is responsible for leaving only the newer version of the plugin
    '''

    if repList and len(repList)>1:     #If the plugin is repeated
        repList.sort(reverse=True)
        print("Repeated plugins found:")
        min=len(repList[0])    # If strings haven't got the same length indicates a change in the numeration version system
        max=min
        newer=datetime.fromtimestamp(0)
        sel=0

        for i,path in enumerate(repList):
            lr=len(path)
            modifDate=datetime.fromtimestamp((os.path.getctime(path)))
            if modifDate>newer:     #Keep the last creation date and its index
                newer=modifDate
                sel=i+1

            if lr<min:
                min=lr
            elif lr>max:
                max=lr

            print(str(i+1) +"" + modifDate.strftime("%Y-%m-%d") +":" + path)
        print("")

        if manual or min!=max:      #If manual mode is enabled or if there is a string length diference between different version of plugins
            selec=raw_input("Which version do you want to keep?: ["+str(sel)+"]")
            if selec:
                selec=int(selec)
            else:
                selec=sel   #Newer is the Default value
        else:
            selec=1


        del(repList[selec-1])      #Delete selected plugin from the list

        for path in repList:  #Move the rest of the list to the backup folder
            print("Deleting:"+ path)
            os.renames(path,os.path.join(dirBackup,os.path.basename(path)))

        print("-------------------------------------

")

def main():

    filePlugins=globRegEx(directory,"^.*$",False,1)      #Creates a list with all the files only
    dirPlugins=globRegEx(directory,"^.*$",False,2)       #Creates a list with all the folders only


    #Process files first

    for plugin in filePlugins:
        m=re.match(r"(.*_)\d.*?\.jar$",plugin)   #Creates the glob pattern
        if m:
            patAux=m.groups()[0]+".*?\.jar$"
            find=globRegEx(directory,patAux,True,1)
            processRepeated(find)

    #Now Directories

    for plugin in dirPlugins:
        m=re.match(r"(.*_)\d.*$",plugin)   #Creates the glob pattern
        if m:
            patAux=m.groups()[0]+".*$"
            find=globRegEx(directory,patAux,True,2)
            processRepeated(find)

if __name__=="__main__":
    main()