$\sum_{i=1}^r \mathcal O(a_i)$ is a sub-bundle of $\sum_{i=1}^s \mathcal O( b_i)$ if and only if, for all $c$, (1) $\# \{ i \mid a_i \geq c \} \leq \# \{i \mid b_i\geq c\}$ and (2) if equality holds for one $c$ it holds for all greater $c$.
Proof of "only if": By twisting, we may assume $c=0$. Then $\sum_{i, a_i\geq 0} \mathcal O(a_i)$ is the maximal globally generated sub-bundle of $\sum_{i=1}^r \mathcal O(a_i)$, thus a sub-bundle of the maximal globally generated sub-bundle $\sum_{i, b_i \geq 0} \mathcal O(b_i)$ of $\sum_{i=1}^s \mathcal O( b_i)$. Hence we have the rank inequality (1) and, if the ranks are equal, the bundles must be isomorphic, giving (2).
Proof of "if": If $V, W$ are two vector bundles, if $V$ is a summand of $W$ then $V \oplus U$ is a summand of $W \oplus U$. Furthermore, our hypothesis holds for $V$ and $W$ (if and) only if holds for $V \oplus U$ and $W \oplus U$. Using this, we may reduce to the case when our two vector bundles have no common direct summand, i.e. when $a_i \neq b_j$ for all $j$.
We may assume the $a_i$ and $b_i$ are in nonincreasing order. In this case, $a_j \leq b_{j+1}$ for all $j$, since if $a_j > b_{j+1}$ then $\#\{ i \mid a_i \geq a_j \} \geq j \geq \# \{ i \mid b_{i} \geq a_j \}$ so by the (1) we have $\#\{ i \mid a_i \geq a_j \} =\# \{ i \mid b_{i} \geq a_j \}$ and then by (2) we have $a_i = b_i $ for all $i \leq j$, contradicting our assumption.
A map $\sum_{i=1}^r \mathcal O(a_i) \to \sum_{i=1}^s \mathcal O(b_i)$ is a matrix $M$ whose entry $M_{ij}$ is a map from $\mathcal O(a_j)$ to $\mathcal O(b_i)$ and thus i section of $\mathcal O(b_i-a_j)$. The matrix has full rank at a point as long as some $r \times r $ minor is nonzero, so the map $V \to W$ is an inclusion of sub-bundles as long as the $r\times r$ minors have no common factors.
We choose a map $M$ such that $M_{ij}=0$ unless $i=j$ or $i={j+1}$. Then the $r\times r$ minor from the first $r$ rows is $\prod_{j=1}^r M_{jj}$ and the $r \times r$ minor from the second $r$ rows is $\prod_{j=1}^r M_{(j+1)j}$. Since $a_j \leq b_{j+1} \leq b_j$ for all $j$, both of these are products of sections of a positive power of $\mathcal O(1)$. We can then take all the $M_{jj}$ to vanish only at $\infty$, and all the $M_{(j+1)j}$ to vanish only at $0$, ensuring these two minors have no common roots, giving an inclusion of sub-bundles, as desired.