Yes and no. You would be
arriving on #49
FROM SYR-CLE on Jan 2, and
departing on #49
FROM CLE-SOB on Jan 2 - so it can be shown it is the same train.
A better example would be CHI-SEA, a trip of 3 days. You leave CHI on Jan 1, but you do not arrive in SEA until Jan 3. True, you could buy a ticket from CHI-MSP on Jan 1 and SPK-SEA on Jan 3, but how do you get between MSP and SPK without a ticket?

I wouldn't want to lose the points for not buying a ticket without my AGR # on it!