Psylocke has all her powers
Current Spidey
Classic Juggs
Psylocke was the only telepath that could mentally attack Juggernaut even with his metal helmet on (as shown in Uncanny X-Men #218).
Will Juggs magical forcefield protect him from psylocke?
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They can win, if Psylocke can mindrape him through the helmet. Otherwise, Spidey and Psylocke are fuxored.
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If he wasn't allowed his forcefield and therefore the helmet could be removed or breached by either Spider-Man or the Psylocke's shadow powers respectively then they could TP him. The Crimson Dawn abilities were magical in nature and allowed Psylocke to teleport through or meld into shadow, although the magic probably isn't strong enough to penetrate Juggernauts magic. So Juggernaut wins.
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Actually I think #218 was prolly close to the Australian X-Men stories, when she was white and had the purple butterfly around her face. I don't think that she was actually able to end the fight however. Then she also did it during Onslaught. She's done it at least twice that I know of.