-Do you wish you had played or worked more during .... not had worked?
-I wish I had listened to my mum and studied harder? not had studied?
You are using what is called a Compound Verb in your sentences, which means two or more verbs connected with "and" and sharing the same subject. Since you are using a verb phrase, which is one or more helping verbs (a.k.a. auxiliary verbs) + a main verb, you may omit the repetition of the helping verb:
I'll italic the subject and bold the Compound Verb.
Do you wish (that) you had played or (had) worked more during... [I placed the understood relative pronoun that to show that a noun dependent clause contains the Compound Verb: you | had played | had worked ]
I wish (that) I had listened to my mum and (had) studied harder.
I can wash windows, clean drapes, and mop floors. [I can wash windows, (can) clean drapes, and (can) mop floors.]
Compound Subject + Compound Verb
Jim and Susan are getting married, buying a car, and eloping to France! [Jim and Susan are getting married, (are ) buying a car, and (are) eloping to France!
The normal sequence is: verb, verb, and verb [you can use all the verbs you want, but leave the comma and the conjunction "and" to the end:
All the girls, including Sarah, played volleyball, swam across the pool, drank too much wine, and fell asleep or passed out (take your pick) on the lawn. How dreadful!
I should say though, you have to watch when using a different sentence structure; yours was a Simple Sentence (one subject and one verb, of which both may be compound). In a Compound Sentence, things can change...
I walked the dog this morning, and my wife walked the dog late this afternoon.
I had spent a couple of nights by Billy's last week, but for the whole of this week, I spent the nights in my own bed. [Two different independent clauses, each having a separate meaning.]
In a Compound Sentence the verb or verbs in each independent clause may or may not be the same, as you can see from the examples.
When you get into Complex Sentences and Compound-Complex Sentences, you have an array of rules governing how verb tense and sequence should go because you now deal with both independent and dependent clauses. Much too long to get into here. Here's a helpful link to a book that covers all the topics here...(see the index for specifics)