When Did Jesus Die the Second Time?

Jesus died only once.  Scripture reminds us that Jesus died “once for all” (Heb. 7:27; 9:27-28).  Some people misunderstand the Sacrifice of the Mass, believing that Catholics re-crucify–or think we believe we re-crucify–Jesus at each and every Mass.  This is seriously mistaken, as Jesus died only once, and the one Sacrifice he offered on our behalf is sacramentally re-presented or made present anew at every Mass (CCC 1366-67.  His one Sacrifice culminated in everlasting glory at his Ascension, and so heaven and earth become profoundly one at every Mass! (cf. CCC 1137-39).
You may be thinking of the “second death” mentioned in Revelation 2:11.  And it’s made clear in Revelation 20:14-15 and 21:7-8 that this second death is the eternal damnation of hell, which those who wilfully and definitively self-exclude themselves from God and his kingdom will suffer (CCC 1033-37).  So, each man and woman dies once and then faces his/her particular judgment (Heb. 9:27; CCC 1021-22), and then either experiences eternal life with God and the angels and saints in heaven, perhaps after being purified in Purgatory (CCC 1030-32; 1023-29), or, God forbid, suffers the second death of eternal hell.