External stimuli can tune the uptake and release of guest molecules in microgels. Especially their pH responsiveness makes microgels exciting candidates for drug delivery systems. When both microgel and guest molecules are pH-responsive, predicting the electrostatically driven uptake can be complex since the ionization depends on many parameters. In this work, we performed Metropolis Monte Carlo simulations while systematically varying the pK of the monomers, the concentrations of microgel and guest molecules to obtain a better understanding of the uptake of weak cationic oligomers as a model for oligopeptides into a weak anionic polyelectrolyte microgel. Further, we varied the chain length of the oligomers. The polyelectrolyte networks can take up oligomers when both the network and the oligomers are charged. The presence of both species in the system leads to a mutual enhancement of their ionization. The uptake induces a release of counterions and results in complex formation between the oligomers and the network, leading to the collapse of the networks. Longer oligomers enhance the ionization of the network and, therefore, the complexation. A higher microgel concentration increases the uptake only around the isoelectric point but prevents the uptake due to lower entropy gain at counterion release at higher pH. The results give an insight into the uptake of cationic oligomers into oppositely charged polyelectrolyte microgels and provide hints for the design of anionic microgels as carriers for guest molecules e.g. antimicrobial peptides.