Can look at this a a problem in binomial expansion of (x+y)^5 which is
x^5 + 5x^4y + 10x^3y^2 +10x^2y^3 +5xy^4 + y^5 with probability of win=0.6 and probability of loss=0.4
The only way they would not win at least one race would be all outcomes except losing 5 times. The probability of 5 loses is (0.4)^5=0.01 so probability of winning at least once is (1.0 - .01 =.99)
For them to win at most 2 races would be the probability of their winning either one or two races
Prob of winning one race is 5(0.6)(0.4)^4- = .0768
Prob of winning two races is 10(0.6)^2(0.4)^3 = .2304
so combined probability = .0768 + .2304 = .3072