I can think of his debut in the Davis Cup which was in the 2002 final when he lost the 5th match to Youzhni after leading 2-0. Yeap, painful, especially since it was at home in Paris-Bercy.
For a teenager that was bad.
Also, a few years later he was axed by Andreev in the DC.
Tiebreak reminded me of FedEx-Roddick Wim 2009, but I gotta say, it's totally different seeing it live, despite the clear differences in importance between the two matches.