Here's one of my favorites: Let's assume playing with a fair coin.
Theorem (false)
In a long coin-tossing game each player will be on the winning side for about half the time, and the lead will pass not infrequently from one player to the other.
The following is from W. Fellers classic of Introduction to Probability Theory and It's Applications, Vol 1:
According to widespread beliefs a so-called law of averages should ensure the Theorem above. But, in fact this theorem is wrong and contrary to the usual belief the following holds:
With probability $\frac{1}{2}$ no equalization occurred in the second half of the game regardless of the length of the game. Furthermore, the probabilities near the end point are greatest.
In fact this leads to the Arc sine law for last visits (see e.g. Vol 1, ch.3, section 4, Theorem 1).
Note: Please note the remarkable statements cited from Chapter III: Fluctuations in Coin Tossing and Random Walks:
For example, in various applications it is assumed, that observations on an individual coin-tossing game during a long time interval will yield the same statistical characteristics as the observation of the results of a huge number of independent games at one given instant. This is not so.
and later on:
Anyhow, it stands to reason that if even the simple coin-tossing game leads to paradoxical results that contradict our intuition, the latter cannot serve as a reliable guide in more complicated situations.
[2015-07-16] According to a comment from @HenningMakholm some examples exposing striking aspects.
Suppose that a great many coin-tossing games are conducted simultaneously at the rate of one per second, day and night, for a whole year. On the average, in one out of ten games the last equalization will occur before $9$ days have passed, and the lead will not change during the following 356 days. In one out of twenty cases the last equalization takes place within $2\frac{1}{2}$ days, and in one out of a hundred cases it
occurs within the first $2$ hours and $10$ minutes.
Suppose that in a learning experiment lasting one year a child was consistently lagging except, perhaps, during the initial week. Another child was consistently ahead except, perhaps, during the last week. Would the two children be judged equal? Yet, let a group of $11$ children be exposed to a similar learning experiment involving no intelligence but only chance. One among the $11$ would appear as leader for all but one week, another as laggard for all but one week.
The examples above are in fact a consequence of the Arc sine law for last visits.