Yes, you are right that the chance of winning at least once is about $40.1\%$. To calculate the probability to win exactly N times in $M$ weeks you have to use the binomial distribution.
$$P(X=N)=\binom{M}{N}\cdot \left(\frac{1}{20} \right)^{N}\cdot \left(\frac{19}{20} \right)^{M-N}$$
Similar for the probability to win at least $N$ times in $M$ weeks is
$$P(X\geq N)=\sum_{k=N}^{M}\binom{M}{k}\cdot \left(\frac{1}{20} \right)^{k}\cdot \left(\frac{19}{20} \right)^{M-k}$$